@article{comins_2022, title={Synthesis of MAPA Reagents and 2-Alkyl(aryl)aminopyridines from 2-Bromopyridine Using the Goldberg Reaction}, volume={27}, ISSN={["1420-3049"]}, DOI={10.3390/molecules27061833}, abstractNote={A short and economical synthesis of various 2-methylaminopyidine amides (MAPA) from 2-bromopyridine has been developed using the catalytic Goldberg reaction. The effective catalyst was formed in situ by the reaction of CuI and 1,10-phenanthroline in a 1/1 ratio with a final loading of 0.5–3 mol%. The process affords high yields and can accommodate multigram-scale reactions. A modification of this method provides a new preparation of 2-N-substituted aminopyridines from various secondary N-alkyl(aryl)formamides and 2-bromopyridine. The intermediate aminopyridine formamide is cleaved in situ through methanolysis or hydrolysis to give 2-alkyl(aryl)aminopyridines in high yields.}, number={6}, journal={MOLECULES}, author={Comins, Daniel L.}, year={2022}, month={Mar} }
 @article{bori_comins_2021, title={Preparation of substituted alkoxypyridines via directed metalation and metal-halogen exchange}, ISSN={["1551-7012"]}, DOI={10.24820/ark.5550190.p011.464}, abstractNote={Several halo-substituted alkoxypyridines were prepared and subjected to directed metalation and metal-halogen exchange reactions. The studies resulted in useful methods for synthesis of numerous substituted pyridines via regioselective lithiation, magnesation and halogen dance reactions}, journal={ARKIVOC}, author={Bori, Ibrahim D. and Comins, Daniel L.}, year={2021}, pages={57–72} }
 @article{comins_ma_2016, title={Editorial for the Special Issue on Heterocycles}, volume={81}, ISSN={["0022-3263"]}, DOI={10.1021/acs.joc.6b02488}, abstractNote={ADVERTISEMENT RETURN TO ISSUEEditorialNEXTEditorial for the Special Issue on HeterocyclesDaniel Comins and Dawei MaView Author Information Department of Chemistry, North Carolina State University Shanghai Institute of Organic ChemistryCite this: J. Org. Chem. 2016, 81, 21, 10107–10108Publication Date (Web):November 4, 2016Publication History Published online4 November 2016Published inissue 4 November 2016https://doi.org/10.1021/acs.joc.6b02488Copyright © 2016 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views835Altmetric-Citations1LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (254 KB) Get e-AlertsSUBJECTS:Addition reactions,Chemical synthesis,Heterocyclic compounds,Organic compounds,Pharmaceuticals Get e-Alerts}, number={21}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Comins, Daniel and Ma, Dawei}, year={2016}, month={Nov}, pages={10107–10108} }
 @article{tsukanov_marks_comins_2016, title={Studies toward the Synthesis of Lepadiformine A}, volume={81}, ISSN={["0022-3263"]}, DOI={10.1021/acs.joc.6b01514}, abstractNote={Herein is described an original approach to access a tricyclic framework of the lepadiformine-type alkaloids. A Grignard/N-acylpyridinium salt reaction of a 4-methoxytetrahydroquinoline is the key carbon-carbon bond-forming step that was used to establish the desired absolute stereochemistry at the C2 position of the target alkaloid. The synthesis features an allylation reaction with an N-acyliminium ion to set the C10 quaternary stereocenter, a mild dissolving-metal cleavage of hindered phenyl carbamates, and an aminoiodocyclization to form the pyrrolidine ring. While this route does not provide the correct C10 stereochemistry, it showcases an efficient method to build analogues with the ring system of this class of alkaloids in 11 steps overall.}, number={21}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Tsukanov, Sergey V. and Marks, Lucas R. and Comins, Daniel L.}, year={2016}, month={Nov}, pages={10433–10443} }
 @article{zhu_enamorado_comins_2016, title={Synthesis of C-4 Substituted Amido Nicotine Derivatives via Copper(I)- and (II)-Catalyzed Cross-Coupling Reactions}, volume={81}, ISSN={["0022-3263"]}, DOI={10.1021/acs.joc.6b02319}, abstractNote={The syntheses of seven novel amido nicotine derivatives 12-18 from (S)-nicotine are presented. (S)-Nicotine and (S)-6-chloronicotine derivatives were cross-coupled with the corresponding amides 6-10 at the C-4 position of the pyridine ring via copper(I)-mediated reactions. Derivatives 16-18 were also obtained via copper(II)-mediated reactions from (S)-nicotine containing a C-4 boronic acid pinacol ester group. The optimization of reaction conditions for both routes provided a useful method for preparing C-4 amide-containing nicotine analogs.}, number={22}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Zhu, Jiancheng and Enamorado, Monica F. and Comins, Daniel L.}, year={2016}, month={Nov}, pages={11529–11534} }
 @article{enamorado_connelly_deiters_comins_2015, title={A concise synthesis of the Lycopodium alkaloid cermizine D}, volume={56}, ISSN={["0040-4039"]}, DOI={10.1016/j.tetlet.2015.04.013}, abstractNote={A racemic and asymmetric synthesis of cermizine D (1) was accomplished in six steps from 4-methoxypyridine or 4-methoxy-3-TIPS-pyridine in 12% and 13% overall yield, respectively. A key step is a stereoselective 1,4-addition of a 2-((trimethylsilyl)methyl)pyridine-derived cuprate to a bicyclic 2,3-dihydro-4-pyridone. Racemic and (−)-cermizine D failed to exhibit cytotoxicity against four different cell lines.}, number={23}, journal={TETRAHEDRON LETTERS}, author={Enamorado, Monica F. and Connelly, Colleen M. and Deiters, Alexander and Comins, Daniel L.}, year={2015}, month={Jun}, pages={3683–3685} }
 @article{hiebel_comins_2015, title={Novel approach toward the morphine skeleton. Synthesis of 1-(5-benzyloxy-2-bromo-4-methoxybenzyl)-6-oxo-3,4,6,7,8,8a-hexahydro-1H-isoquinoline-2-carboxylic acid phenyl ester via N-acylpyridinium salt chemistry}, volume={71}, ISSN={["0040-4020"]}, DOI={10.1016/j.tet.2015.04.086}, abstractNote={A dihydropyridone-mediated approach to the morphine skeleton was investigated. The hexahydroisoquinoline 2 was synthesized in nine steps using N-acylpyridinium chemistry and dihydropyridone functionalization methods. This new approach should be useful in the design of more efficient syntheses of morphine and its derivatives.}, number={39}, journal={TETRAHEDRON}, author={Hiebel, Anne-Cecile and Comins, Daniel L.}, year={2015}, month={Sep}, pages={7354–7360} }
 @article{neufeldt_jimenez-oses_comins_houk_2014, title={A Twist on Facial Selectivity of Hydride Reductions of Cyclic Ketones: Twist-Boat Conformers in Cyclohexanone, Piperidone, and Tropinone Reactions}, volume={79}, ISSN={["1520-6904"]}, DOI={10.1021/jo5022635}, abstractNote={The role of twist-boat conformers of cyclohexanones in hydride reductions was explored. The hydride reductions of a cis-2,6-disubstituted N-acylpiperidone, an N-acyltropinone, and tert-butylcyclohexanone by lithium aluminum hydride and by a bulky borohydride reagent were investigated computationally and compared to experiment. Our results indicate that in certain cases, factors such as substrate conformation, nucleophile bulkiness, and remote steric features can affect stereoselectivity in ways that are difficult to predict by the general Felkin–Anh model. In particular, we have calculated that a twist-boat conformation is relevant to the reactivity and facial selectivity of hydride reduction of cis-2,6-disubstituted N-acylpiperidones with a small hydride reagent (LiAlH4) but not with a bulky hydride (lithium triisopropylborohydride).}, number={23}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Neufeldt, Sharon R. and Jimenez-Oses, Gonzalo and Comins, Daniel L. and Houk, K. N.}, year={2014}, month={Dec}, pages={11609–11618} }
 @article{cash_prevost_wagner_comins_2014, title={Studies toward the Total Synthesis of Dihydrolycolucine. Preparation of AB and CEF Ring Fragments}, volume={79}, ISSN={["0022-3263"]}, DOI={10.1021/jo500878v}, abstractNote={A strategy for the synthesis of the lycopodium alkaloid dihydrolycolucine (1) has been investigated. Synthetic routes were developed based on N-acylpyridinium salt chemistry to prepare target fragments 3 and 4 that could ultimately converge to the natural product. Key reactions include IMDA cycloadditions and retro-Mannich ring-openings to form both the AB and the EF ring fragments. The ring C precursor was prepared using pyridine substitution and directed lithiation chemistry. A Suzuki cross-coupling of rings C and EF led to the CEF ring fragment. Initial attempts at closure of the seven-membered D ring were unsuccessful.}, number={12}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Cash, Brandon M. and Prevost, Natacha and Wagner, Florence F. and Comins, Daniel L.}, year={2014}, month={Jun}, pages={5740–5745} }
 @article{tsukanov_comins_2014, title={Total Synthesis of Alkaloid 205B}, volume={79}, ISSN={["0022-3263"]}, DOI={10.1021/jo501415r}, abstractNote={Concise and highly stereocontrolled total syntheses of racemic and enantiopure frog alkaloid 205B (1) were accomplished in 11 steps from 4-methoxypyridines 6 and 7 in overall yields of 8 and 8%, respectively. The assembly of the core of the natural product relies on a stereoselective Tsuji–Trost allylic amination reaction and a ring-closing metathesis. The synthesis features the use of an N-acylpyridinium salt reaction to introduce the first stereocenter and an unprecedented trifluoroacetic anhydride-mediated addition of an allylstannane to a vinylogous amide with complete facial selectivity. Deoxygenation of the C4 ketone proved difficult but was accomplished via a modified Barton–McCombie reaction in the presence of a catalytic amount of diphenyl diselenide.}, number={19}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Tsukanov, Sergey V. and Comins, Daniel L.}, year={2014}, month={Oct}, pages={9074–9085} }
 @misc{comins_higuchi_young_2013, title={Dihydropyridine preparation and application in the synthesis of pyridine derivatives}, volume={110}, journal={Advances in heterocyclic chemistry, vol 110}, author={Comins, D. L. and Higuchi, K. and Young, D. W.}, year={2013}, pages={175–235} }
 @article{sahn_bharathi_comins_2012, title={Studies toward the synthesis of spirolucidine. Preparation of ABC and EF ring fragments}, volume={53}, ISSN={["0040-4039"]}, DOI={10.1016/j.tetlet.2011.12.127}, abstractNote={ABC and EF ring fragments of spirolucidine have been prepared via asymmetric synthesis using chiral N-acylpyridinium salt chemistry. Model studies have been carried out to support further progress toward the completion of this complex alkaloid.}, number={11}, journal={TETRAHEDRON LETTERS}, author={Sahn, James J. and Bharathi, Pandi and Comins, Daniel L.}, year={2012}, month={Mar}, pages={1347–1350} }
 @article{tsukanov_comins_2011, title={Concise Total Synthesis of the Frog Alkaloid (-)-205B}, volume={50}, ISSN={["1433-7851"]}, DOI={10.1002/anie.201103596}, abstractNote={Highly stereocontrolled: The total synthesis of frog alkaloid (−)-205B features a chiral N-acylpyridinium salt reaction and an unprecedented trifluoroacetic anhydride mediated addition of an allylstannane to a vinylogous amide. The core was assembled using a Tsuji–Trost allylic amination reaction and a ring-closing metathesis. TIPS=triisopropylsilyl. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.}, number={37}, journal={ANGEWANDTE CHEMIE-INTERNATIONAL EDITION}, author={Tsukanov, Sergey V. and Comins, Daniel L.}, year={2011}, pages={8626–8628} }
 @article{walker_lilley_enamorado_comins_muddiman_2011, title={Hydrophobic Derivatization of N-linked Glycans for Increased Ion Abundance in Electrospray Ionization Mass Spectrometry}, volume={22}, ISSN={["1044-0305"]}, DOI={10.1007/s13361-011-0140-x}, abstractNote={A library of neutral, hydrophobic reagents was synthesized for use as derivatizing agents in order to increase the ion abundance of N-linked glycans in electrospray ionization mass spectrometry (ESI MS). The glycans are derivatized via hydrazone formation and are shown to increase the ion abundance of a glycan standard more than 4-fold. Additionally, the data show that the systematic addition of hydrophobic surface area to the reagent increases the glycan ion abundance, a property that can be further exploited in the analysis of glycans. The results of this study will direct the future synthesis of hydrophobic reagents for glycan analysis using the correlation between hydrophobicity and theoretical non-polar surface area calculation to facilitate the development of an optimum tag for glycan derivatization. The compatibility and advantages of this method are demonstrated by cleaving and derivatizing N-linked glycans from human plasma proteins. The ESI-MS signal for the tagged glycans are shown to be significantly more abundant, and the detection of negatively charged sialylated glycans is enhanced.}, number={8}, journal={JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY}, author={Walker, S. Hunter and Lilley, Laura M. and Enamorado, Monica F. and Comins, Daniel L. and Muddiman, David C.}, year={2011}, month={Aug}, pages={1309–1317} }
 @article{watson_motsinger-reif_hardison_peters_havener_everitt_auman_comins_mcleod_2011, title={Identification and replication of loci involved in camptothecin-induced cytotoxicity using CEPH pedigrees}, volume={6}, number={5}, journal={PLoS One}, author={Watson, V. G. and Motsinger-Reif, A. and Hardison, N. E. and Peters, E. J. and Havener, T. M. and Everitt, L. and Auman, J. T. and Comins, D. L. and McLeod, H. L.}, year={2011} }
 @article{enamorado_ondachi_comins_2010, title={A Five-Step Synthesis of (S)-Macrostomine from (S)-Nicotine}, volume={12}, ISSN={["1523-7052"]}, DOI={10.1021/ol101887b}, abstractNote={A concise synthesis of (S)-macrostomine has been accomplished in five steps from natural nicotine in 19% overall yield via a pyridyne Diels-Alder cycloaddition reaction as the key step. A Kumada cross-coupling reaction on a 1-chloroisoquinoline intermediate provided the natural product.}, number={20}, journal={ORGANIC LETTERS}, author={Enamorado, Monica F. and Ondachi, Pauline W. and Comins, Daniel L.}, year={2010}, month={Oct}, pages={4513–4515} }
 @article{wolfe_libby_al-awar_foti_comins_2010, title={Asymmetric Synthesis of All the Known Phlegmarine Alkaloids}, volume={75}, ISSN={["0022-3263"]}, DOI={10.1021/jo1019688}, abstractNote={The asymmetric synthesis of all four of the known natural phlegmarines and one synthetic derivative has been accomplished in 19-22 steps from 4-methoxy-3-(triisopropylsilyl)pyridine. Chiral N-acylpyridinium salt chemistry was used twice to set the stereocenters at the C-9 and C-2' positions of the phlegmarine skeleton. Key reactions include the use of a mixed Grignard reagent for the second N-acylpyridinium salt addition, zinc/acetic acid reduction of a complex dihydropyridone, and a von Braun cyanogen bromide N-demethylation of a late intermediate. These syntheses confirmed the absolute stereochemistry of all of the known phlegmarines.}, number={24}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Wolfe, Bradley H. and Libby, Adam H. and Al-awar, Rima S. and Foti, Christopher J. and Comins, Daniel L.}, year={2010}, month={Dec}, pages={8564–8570} }
 @article{shuford_comins_whitten_burnett_muddiman_2010, title={Improving limits of detection for B-type natriuretic peptide using PC-IDMS: An application of the ALiPHAT strategy}, volume={135}, ISSN={["1364-5528"]}, DOI={10.1039/b919484c}, abstractNote={Hydrophobic tagging of biomolecules has been reported by our group and others to increase their ionization efficiency during electrospray ionization and facilitate their detection by mass spectrometry. As such, hydrophobic tagging should provide a viable method for augmenting MS-based quantification of low abundance proteins by decreasing their detection limits. Herein we have evaluated two commercial alkylation reagents and several newly synthesized hydrophobic alkylation reagents for their utility in quantifying B-type Natriuretic Peptide, a low abundance cardiac biomarker, by protein cleavage isotope dilution mass spectrometry. For the cysteine containing tryptic peptide evaluated, a approximately 3.5-fold decrease in the detection limit was observed for the best performing hydrophobic reagent, 2-iodo-N-octylacetamide, relative to the commonly used alkylation reagent, iodoacetamide. Additionally, we have evaluated the use of nonpolar surface areas as a metric for assessing the effectiveness of the alkylation reagents in improving ESI response.}, number={1}, journal={ANALYST}, author={Shuford, Christopher M. and Comins, Daniel L. and Whitten, Jerry L. and Burnett, John C., Jr. and Muddiman, David C.}, year={2010}, pages={36–41} }
 @article{bereman_comins_muddiman_2010, title={Increasing the hydrophobicity and electrospray response of glycans through derivatization with novel cationic hydrazides}, volume={46}, ISSN={["1364-548X"]}, DOI={10.1039/b915589a}, abstractNote={Novel tags are used to increase the hydrophobicity of glycans and impart a permanent charge yielding as great as a approximately 5-fold increase in electrospray response from both a standard and complex mixture.}, number={2}, journal={CHEMICAL COMMUNICATIONS}, author={Bereman, Michael S. and Comins, Daniel L. and Muddiman, David C.}, year={2010}, pages={237–239} }
 @article{walker_papas_comins_muddiman_2010, title={Interplay of Permanent Charge and Hydrophobicity in the Electrospray Ionization of Glycans}, volume={82}, ISSN={["1520-6882"]}, DOI={10.1021/ac101227a}, abstractNote={The analysis of N-linked glycans by mass spectrometry (MS) has been characterized by low signal-to-noise ratios and high limits of detection due to their hydrophilicity and lack of basic sites able to be protonated. As a result, every step in glycan sample preparation must be thoroughly optimized in order to minimize sample loss, contamination, and analytical variability. Importantly, properties of glycans and their derivatized counterparts must be thoroughly studied in order to exploit certain characteristics for enhancing MS analysis. Herein, the effectiveness of the incorporation of a permanent charge is studied and determined to hamper glycan analysis. Also, a procedure for glycan hydrazone formation is optimized and outlined where a large number of variables were simultaneously analyzed using a fractional factorial design (FFD) in order to determine which conditions affected the reaction efficiency of the hydrazone formation reaction. Finally, the hydrophobic tagging of glycans is shown to be a viable opportunity to further increase the ion abundance of glycans in MS.}, number={15}, journal={ANALYTICAL CHEMISTRY}, author={Walker, S. Hunter and Papas, Brian N. and Comins, Daniel L. and Muddiman, David C.}, year={2010}, month={Aug}, pages={6636–6642} }
 @misc{king_smith_comins_2010, title={Regiospecific synthesis of nicotine derivatives}, volume={7,671,209}, number={2010 Mar. 2}, author={King, L. S. and Smith, E. and Comins, D. L.}, year={2010} }
 @article{ondachi_comins_2010, title={Synthesis of Fused-Ring Nicotine Derivatives from (S)-Nicotine}, volume={75}, ISSN={["0022-3263"]}, DOI={10.1021/jo9026929}, abstractNote={The synthesis of novel fused-ring bicyclic (4-6) and tricyclic (7-10) nicotine derivatives from natural (S)-nicotine are described. Enantiopure bicyclic dioxino, dihydrofuro, and dihydropyranol nicotine derivatives as well as tricylic benzofuro and benzopyran derivatives were synthesized from simple alkoxy or halonicotine intermediates. Attempts to synthesize furonicotines (11, 12) resulted in formation of the furonicotine dimers 42 and 49.}, number={5}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Ondachi, Pauline W. and Comins, Daniel L.}, year={2010}, month={Mar}, pages={1706–1716} }
 @article{sahn_comins_2010, title={[2+2] Photochemical Cycloaddition/Ring Opening of 6-Alkenyl-2,3-dihydro-4-pyridones}, volume={75}, ISSN={["0022-3263"]}, DOI={10.1021/jo101276q}, abstractNote={During the course of a study aimed at constructing azaspirocycles from 2,3-dihydro-4-pyridones, an unexpected product was obtained in the SET ring-opening reaction of photocycloadduct 1. Differences in reactivity between homologues 1 and 2 were observed in the presence of SmI(2). Tricyclic ketone 2 afforded azaspiro[5.5]undecane 15 when treated with SmI(2); however, when ketone 1 was submitted to similar reaction conditions a double ring-opening/reduction sequence gave cis-piperidinol 10.}, number={19}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Sahn, James J. and Comins, Daniel L.}, year={2010}, month={Oct}, pages={6728–6731} }
 @article{capracotta_comins_2009, title={Chiral amino alcohols derived from (S)-6-chloronicotine as catalysts for asymmetric synthesis}, volume={50}, ISSN={["0040-4039"]}, DOI={10.1016/j.tetlet.2009.02.012}, abstractNote={Commercially available (S)-nicotine was converted in two or three synthetic steps to various chiral amino alcohols. These nicotine derivatives were evaluated as potential chiral ligands for metal-catalyzed asymmetric reactions by using the addition of diethylzinc to aldehydes as a screen. Several reactions proceeded with a high degree of enantioselectivity providing good yields of secondary alcohols of high enantiopurity.}, number={16}, journal={TETRAHEDRON LETTERS}, author={Capracotta, Sonja S. and Comins, Daniel L.}, year={2009}, month={Apr}, pages={1806–1808} }
 @article{williams_comins_whitten_muddiman_2009, title={Evaluation of the ALiPHAT Method for PC-IDMS and Correlation of Limits-of-Detection with Nonpolar Surface Area}, volume={20}, ISSN={["1879-1123"]}, DOI={10.1016/j.jasms.2009.07.019}, abstractNote={PC-IDMS experiments for two peptides, laminin nonapeptide and the N-terminal tryptic peptide of prostate specific antigen, were performed utilizing a variety of alkylating reagents. These experiments were conducted to investigate how hydrophobicity influences the limits-of-detection (LOD) by altering their electrospray ionization response. Nonpolar surface areas were calculated for both peptides and all alkylating reagents to provide an estimate of the hydrophobicity of the differently alkylated peptides. Decreases in LOD by 2-fold were observed for both peptides between the best and worst performing combination of alkylating reagent. However, while an increase in hydrophobicity was found to aid in decreasing LOD to an extent, beyond a certain hydrophobicity, we observed a decrease.}, number={11}, journal={JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY}, author={Williams, D. Keith, Jr. and Comins, Daniel L. and Whitten, Jerry L. and Muddiman, David C.}, year={2009}, month={Nov}, pages={2006–2012} }
 @article{mccall_comins_2009, title={Synthesis of 1,3-Amino Alcohol Derivatives via a Silicon-Mediated Ring-Opening of Substituted Piperidines}, volume={11}, ISSN={["1523-7052"]}, DOI={10.1021/ol9010757}, abstractNote={Multisubstituted piperidines containing a trimethylsilylmethyl group at C-2 can be opened regioselectively with TBAF and cyanogen bromide. The ring-opened products contain synthetically useful cyanamide and terminal alkene functional groups. This method is useful for the stereoselective synthesis of alkylamine derivatives containing multiple chiral centers.}, number={13}, journal={ORGANIC LETTERS}, author={McCall, W. Stephen and Comins, Daniel L.}, year={2009}, month={Jul}, pages={2940–2942} }
 @misc{comins_smith_2009, title={Synthesis of nicotine derivatives from nicotine}, volume={7,553,968}, number={2009 Jun 30}, author={Comins, D. L. and Smith, E. D.}, year={2009} }
 @article{bharathi_comins_2008, title={Asymmetric synthesis of C-2-symmetric vicinal diamines via reductive dimerization of N-acylpyridinium and related salts}, volume={10}, ISSN={["1523-7052"]}, DOI={10.1021/ol702595d}, abstractNote={A new route to C2-symmetric diamines via an asymmetric reductive dimerization of 1-acylpyridinium salts and their benzo derivatives is described. This method is practical as the starting heterocycles and chiral auxiliaries are readily available. The titanium reducing agent is inexpensive and easy to prepare. Several novel enantiopure C2-symmetric diamine derivatives were synthesized using this method.}, number={2}, journal={ORGANIC LETTERS}, author={Bharathi, Pandi and Comins, Daniel L.}, year={2008}, month={Jan}, pages={221–223} }
 @article{eliyahu_nojima_capracotta_comins_schal_2008, title={Identification of cuticular lipids eliciting interspecific courtship in the German cockroach, Blattella germanica}, volume={95}, ISSN={["1432-1904"]}, DOI={10.1007/s00114-007-0339-7}, abstractNote={The cuticular surface of sexually mature females of the German cockroach contains a sex pheromone that, upon contact with the male's antennae, elicits a characteristic species-specific courtship behavior. This female-specific pheromone is a blend of several long-chain methyl ketones, alcohols and aldehydes, all derived from prominent cuticular hydrocarbons found in all life stages of this cockroach. We found that contact with the antennae of 5 out of 20 assayed cockroach species elicited courtship behavior in German cockroach males. The heterospecific courtship-eliciting compounds were isolated by behaviorally guided fractionation of the active crude extracts and compared to the native sex pheromone components. We identified two active compounds from the cuticular extract of the Oriental cockroach, Blatta orientalis -- 11-methylheptacosan-2-one and 27-oxo-11-methylheptacosan-2-one; the former compound was confirmed by synthesis and proved to independently stimulate courtship in German cockroach males. These compounds share common features with, but are distinct from, any of the known contact sex pheromone components. This suggests that sex pheromone reception in the male German cockroach is unusually promiscuous, accepting a wide range of compounds that share certain features with its native pheromone, thus resulting in a broad spectrum of behavioral response to other species. We propose that several characteristics of their mating system -- chiefly, absence of closely related species in the anthropogenic environment, resulting in relaxation of selection on sexual communication, and a highly male-biased operational sex ratio -- have driven males to respond with extremely low thresholds to a wide spectrum of related compounds.}, number={5}, journal={NATURWISSENSCHAFTEN}, author={Eliyahu, Dorit and Nojima, Satoshi and Capracotta, Sonja S. and Comins, Daniel L. and Schal, Coby}, year={2008}, month={May}, pages={403–412} }
 @article{mccall_grillo_comins_2008, title={N-Acyldihydropyridones as Synthetic Intermediates. A Stereoselective Synthesis of Acyclic Amino Alcohols Containing Multiple Chiral Centers}, volume={73}, ISSN={["0022-3263"]}, DOI={10.1021/jo802029y}, abstractNote={Various multisubstituted piperidines containing a phenyl group at C-2 can be opened regio- and stereoselectively with cyanogen bromide. The ring-opened products contain useful cyanamide and benzylic bromide functional groups. The benzyl bromide can be cleanly reduced, or substituted with various nucleophiles via an S(N)2 process to add additional heteroatoms stereoselectively. This methodology is useful for the stereoselective synthesis of uniquely substituted alkylamine derivatives containing multiple chiral centers and various functionality. Diastereomerically pure amino alcohols containing three to five contiguous stereocenters were prepared using this strategy.}, number={24}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={McCall, W. Stephen and Grillo, Teresa Abad and Comins, Daniel L.}, year={2008}, month={Dec}, pages={9744–9751} }
 @article{mccall_grillo_comins_2008, title={Stereoselective synthesis of acyclic amino alcohols via von Braun ring opening of chiral piperidines}, volume={10}, ISSN={["1523-7052"]}, DOI={10.1021/ol801123x}, abstractNote={Multisubstituted piperidines containing a phenyl group at C-2 can be opened regio- and stereoselectively with cyanogen bromide. The ring-opened products contain useful cyanamide and benzylic bromide functional groups. This methodology is useful for the stereoselective synthesis of uniquely substituted alkylamine derivatives containing multiple chiral centers and various functionality.}, number={15}, journal={ORGANIC LETTERS}, author={McCall, W. Stephen and Grillo, Teresa Abad and Comins, Daniel L.}, year={2008}, month={Aug}, pages={3255–3257} }
 @article{ondachi_comins_2008, title={Synthesis and regioselective substitution of C-6 alkoxy derivatives of (S)-nicotine}, volume={49}, ISSN={["0040-4039"]}, DOI={10.1016/j.tetlet.2007.11.041}, abstractNote={Enantiopure (S)-6-alkoxynicotine derivatives have been synthesized in two steps from (S)-nicotine via (S)-6-iodonicotine. Deprotonation and substitution at the C-5 position of the pyridine ring of (S)-6-methoxynicotine were achieved using mesityllithium as the base at 0 °C. Conditions for the C-4 lithiation/substitution of (S)-6-isopropoxynicotine and (S)-5-chloro-6-methoxynicotine were also developed.}, number={3}, journal={TETRAHEDRON LETTERS}, author={Ondachi, Pauline W. and Comins, Daniel L.}, year={2008}, month={Jan}, pages={569–572} }
 @misc{comins_d._2008, title={Synthesis of nicotine derivatives from nicotine}, volume={7,361,768}, number={2008 Apr. 22}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and D., Smith E.}, year={2008} }
 @article{williams_meadows_bori_hawkridge_comins_muddiman_2008, title={Synthesis, characterization, and application of lodoacetamide derivatives utilized for the ALiPHAT strategy}, volume={130}, DOI={10.1021/jao076849y}, number={7}, journal={Journal of the American Chemical Society}, author={Williams, D. K. and Meadows, C. W. and Bori, I. D. and Hawkridge, A. M. and Comins, D. L. and Muddiman, David}, year={2008}, pages={2122-} }
 @article{frahm_bori_comins_hawkridge_muddiman_2007, title={Achieving augmented limits of detection for peptides with hydrophobic alkyl tags}, volume={79}, ISSN={["0003-2700"]}, DOI={10.1021/ac070558q}, abstractNote={The wide range of protein concentrations found in biological matrixes presents a formidable analytical challenge in proteomics experiments. It is predicted that low-abundance proteins are the likely clinically relevant targets in disease-based proteomics analyses. To effectively analyze low-abundance proteins by electrospray ionization mass spectrometry, limits of detection must be improved upon. Previous studies have demonstrated hydrophobicity is a main determinant of the electrospray ionization response. One would expect to improve the electrospray ionization response of a hydrophilic peptide by making it more hydrophobic, thus increasing the molecule's affinity for the surface of the electrospray droplet, thereby allowing the molecule to more effectively compete for charge. In this report, we demonstrate a strategy to increase the electrospray ionization response of cysteine-containing peptides with the addition of an octylcarboxyamidomethyl modification via alkylation chemistry, which we name the ALiPHAT strategy (augmented limits of detection for peptides with hydrophobic alkyl tags). We demonstrate the relative increase in electrospray ionization response of peptides with an octylcarboxyamidomethyl modification compared to carboxyamidomethyl-modified peptides upon LC-MS analysis. Furthermore, we show the octylcarboxyamidomethyl group does not fragment or undergo neutral loss during collision-induced dissociation. Collectively, our results demonstrate the feasibility of the octylcarboxyamidomethyl modification to improve limits of detection for cysteine-containing peptides.}, number={11}, journal={ANALYTICAL CHEMISTRY}, author={Frahm, Jennifer L. and Bori, Ibrahim D. and Comins, Daniel L. and Hawkridge, Adam M. and Muddiman, David C.}, year={2007}, month={Jun}, pages={3989–3995} }
 @article{stumpf_comins_sparks_donohue_roe_2007, title={Insecticidal activity and mode of action of novel nicotinoids synthesized by new acylpyridinium salt chemistry and directed lithiation}, volume={87}, ISSN={["1095-9939"]}, DOI={10.1016/j.pestbp.2006.07.012}, abstractNote={Novel acylpyridinium salt chemistry and directed lithiation methodology was developed to add for the first time substitutions directly to the phenylpyridine heterocyclic ring of nicotine. A variety of 3-(1-methylpyrrolidin-2-yl)-4-(alkyl, aromatic, heterocyclic and silanyl) and -N-alkyl pyridines were synthesized (compounds 1–9). In vial tests with the green peach aphid, Myzus persicae, compounds 1–4 were 1.1, 1.8, 2.3 and 1.9×, respectively, more active than nicotine and 64, 40, 31 and 38×, respectively, less active than acetamiprid. Against the western flower thrips, Frankliniella occidentalis, 1–4 were 1.4, 2.1, 2.0 and 1.6×, respectively, more active than nicotine and 9, 6, 6 and 8×, respectively, less active than acetamiprid. For the cotton aphid, Aphis gossypii, the activity of 1–9 was similar to nicotine. Compounds 7 and 9 when incorporated into artificial diet produced low mortality for larvae of the beet armyworm, Spodoptera exigua, but were not active against the corn earworm, Helicoverpa zea. When 1–4 and 6–9 were injected into larvae of the beet armyworm, a variety of symptoms similar to acetamiprid were observed which included tremors, uncoordinated movement, diuresis, paralysis and death. In addition, imidacloprid-binding to membranes from the house fly head, Musca domestica, was inhibited by compounds 1–9, when using a concentration range of 1–100 μM. These studies demonstrate that our new chemistry enhances the insecticidal activity of nicotine with an apparent mode of action as an acetylcholine agonist.}, number={3}, journal={PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY}, author={Stumpf, Christof F. and Comins, Daniel L. and Sparks, Thomas C. and Donohue, Kevin V. and Roe, R. Michael}, year={2007}, month={Mar}, pages={211–219} }
 @article{comins_dinsmore_marks_2007, title={One-pot terminal alkene homologation using a tandem olefin cross-metathesis/allylic carbonate reduction sequence}, ISSN={["1359-7345"]}, DOI={10.1039/b709754a}, abstractNote={A one-carbon homologation of terminal alkenes has been developed utilizing an olefin cross-metathesis followed by a palladium-mediated allylic carbonate reduction; various substrates were used to demonstrate the scope of the reaction, with yields ranging from 65 to 86%.}, number={40}, journal={CHEMICAL COMMUNICATIONS}, author={Comins, Daniel L. and Dinsmore, Jason M. and Marks, Lucas R.}, year={2007}, pages={4170–4171} }
 @article{wagner_comins_2007, title={Recent advances in the synthesis of nicotine and its derivatives}, volume={63}, ISSN={["0040-4020"]}, DOI={10.1016/j.tet.2007.04.100}, abstractNote={This review covers developments in the synthesis of nicotine and derivatives published mainly from 1996 to 2006.}, number={34}, journal={TETRAHEDRON}, author={Wagner, Florence F. and Comins, Daniel L.}, year={2007}, month={Aug}, pages={8065–8082} }
 @misc{comins_fevrier_smith_2007, title={Regioselective halogenation of nicotine and substituted nicotines}, volume={7,179,917}, number={2007 Feb. 20}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Fevrier, F. and Smith, E. D.}, year={2007} }
 @misc{king_smith_comins_2007, title={Regiospecific synthesis of nicotine derivatives}, volume={7,304,160}, number={2007 Dec. 4}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={King, L. S. and Smith, E. and Comins, D. L.}, year={2007} }
 @article{comins_higuchi_2007, title={Synthesis of the benzo-fused indolizidine alkaloid mimics}, volume={3}, journal={Beilstein Journal of Organic Chemistry}, author={Comins, D. L. and Higuchi, K.}, year={2007} }
 @article{comins_smith_2006, title={A six-step synthesis of (S)-5-ethenyl-3-(1-methy1-2-pyrrolidinyl)pyridine (SIB-1508Y) from (S)-nicotine}, volume={47}, ISSN={["0040-4039"]}, DOI={10.1016/j.tetlet.2005.12.085}, abstractNote={The anti-Parkinson’s agent SIB-1508Y was prepared in six steps from (S)-nicotine in 20% overall yield. The strategy involves a regioselective formylation at C-5 of a 1,4-dihydronicotine intermediate.}, number={9}, journal={TETRAHEDRON LETTERS}, author={Comins, DL and Smith, ED}, year={2006}, month={Feb}, pages={1449–1451} }
 @article{wagner_comins_2006, title={Expedient five-step synthesis of SIB-1508Y from natural nicotine}, volume={71}, ISSN={["0022-3263"]}, DOI={10.1021/jo0616052}, abstractNote={Altinicline (SIB-1508Y), an anti-Parkinson's agent, was prepared in five steps from natural nicotine in 32% overall yield via a regioselective substitution of the pyridine ring of (S)-nicotine.}, number={22}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Wagner, Florence F. and Comins, Daniel L.}, year={2006}, month={Oct}, pages={8673–8675} }
 @article{wagner_comins_2006, title={Regioselective 5-, 4-, and 2-substitution of (S)-6-chloronicotine and 4-substitution of (S)-5-chloronicotine}, volume={2006}, ISSN={["1099-0690"]}, DOI={10.1002/ejoc.200600415}, abstractNote={Abstract}, number={16}, journal={EUROPEAN JOURNAL OF ORGANIC CHEMISTRY}, author={Wagner, Florence F. and Comins, Daniel L.}, year={2006}, month={Aug}, pages={3562–3565} }
 @misc{comins_fevrier_smith_2006, title={Regioselective halogenation of nicotine and substituted nicotines}, volume={7,067,672}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Fevrier, F. and Smith, E. D.}, year={2006} }
 @misc{king_smith_comins_2006, title={Regiospecific synthesis of nicotine derivatives}, volume={7,112,678}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={King, L. S. and Smith, E. and Comins, D. L.}, year={2006} }
 @misc{comins_huang_2006, title={Short synthesis of pyridine-based pharmaceutical intermediates}, volume={6,987,189}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Huang, S.}, year={2006} }
 @article{wagner_comins_2006, title={Six-step synthesis of (S)-brevicolline from (S)-nicotine}, volume={8}, ISSN={["1523-7060"]}, DOI={10.1021/ol061334h}, abstractNote={[reaction: see text] A six-step synthesis of (S)-brevicolline from (S)-nicotine is reported. Regioselective trisubstitution of the pyridine ring of nicotine, followed by successive Suzuki cross-coupling and Buchwald amination reactions, afforded the enantiopure beta-carboline alkaloid, brevicolline.}, number={16}, journal={ORGANIC LETTERS}, author={Wagner, Florence F. and Comins, Daniel L.}, year={2006}, month={Aug}, pages={3549–3552} }
 @misc{comins_smith_2006, title={Synthesis of nicotine derivatives from nicotine}, volume={6,995,265}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Smith, E. D.}, year={2006} }
 @article{smith_fevrier_comins_2006, title={Synthesis of nicotine derivatives via reductive disilylation of (S)-nicotine}, volume={8}, ISSN={["1523-7052"]}, DOI={10.1021/ol052099q}, abstractNote={[reaction: see text] A variety of novel nicotine derivatives were prepared via reductive disilylation of (S)-nicotine. Treatment of nicotine with lithium powder and chlorotrimethylsilane afforded 1,4-bis(trimethylsilyl)-1,4-dihydronicotine in high yield. Addition of various carbonyl electrophiles and a catalytic amount of TBAF provided either C-5 substituted nicotines or 1,4-dihydronicotine derivatives.}, number={2}, journal={ORGANIC LETTERS}, author={Smith, ED and Fevrier, FC and Comins, DL}, year={2006}, month={Jan}, pages={179–182} }
 @article{gotchev_comins_2006, title={Synthetic studies toward (-)-FR901483 using a conjugate allylation to install the C-1 quaternary carbon}, volume={71}, ISSN={["1520-6904"]}, DOI={10.1021/jo061677t}, abstractNote={Two approaches to the aza-tricyclo dodecane skeleton of (-)-FR901483 are reported. Both routes utilized a Grignard addition to an N-acylpyridinium salt to establish the absolute stereochemistry at C-6 and a highly diastereoselective conjugate allylation reaction to form the quaternary center at C-1 of the natural product in an excellent yield. Although the desired polysubstituted piperidine intermediates were prepared regio- and stereoselectively, the construction of the C-8/C-9 bond connectivity could not be achieved. All attempts at a pinacol cyclization or an intramolecular 6-exo-tet epoxide opening were unsuccessful because of an unfavorable A(1,3) strain inherent in the molecule.}, number={25}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Gotchev, Dimitar B. and Comins, Daniel L.}, year={2006}, month={Dec}, pages={9393–9402} }
 @article{comins_sahn_2005, title={A six-step asymmetric synthesis of (+)-hyperaspine}, volume={7}, ISSN={["1523-7052"]}, DOI={10.1021/ol052068v}, abstractNote={ADVERTISEMENT RETURN TO ISSUEPREVLetterNEXTA Six-Step Asymmetric Synthesis of (+)-HyperaspineDaniel L. Comins and James J. SahnView Author Information Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204 Cite this: Org. Lett. 2005, 7, 23, 5227–5228Publication Date (Web):October 21, 2005Publication History Received26 August 2005Published online21 October 2005Published inissue 1 November 2005https://doi.org/10.1021/ol052068vCopyright © 2005 American Chemical SocietyRequest reuse permissionsArticle Views1383Altmetric-Citations44LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (39 KB) Get e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Alcohols,Enantioselective synthesis,Ketones,Redox reactions Get e-Alerts}, number={23}, journal={ORGANIC LETTERS}, author={Comins, DL and Sahn, JJ}, year={2005}, month={Nov}, pages={5227–5228} }
 @article{comins_hiebel_2005, title={Asymmetric synthesis of 3,3-disubstituted isoindolinones}, volume={46}, ISSN={["0040-4039"]}, DOI={10.1016/j.tetlet.2005.06.105}, abstractNote={An anionic chiral auxiliary-mediated asymmetric alkylation of carbamate 2 affords 3,3-disubstituted isoindolinones 3 in moderate to high de. The chiral auxiliary can be removed and recovered under mild conditions, and the resulting enantiopure lactams further elaborated.}, number={34}, journal={TETRAHEDRON LETTERS}, author={Comins, DL and Hiebel, AU}, year={2005}, month={Aug}, pages={5639–5642} }
 @article{comins_schilling_zhang_2005, title={Asymmetric synthesis of 3-substituted isoindolinones: Application to the total synthesis of (+)-lennoxamine}, volume={7}, ISSN={["1523-7060"]}, DOI={10.1021/ol047824w}, abstractNote={An anionic chiral auxiliary mediated asymmetric alkylation of carbamate 2 provides 3-substituted isoindolinones 4 in high ee. This methodology was used in the first asymmetric synthesis of (+)-lennoxamine.}, number={1}, journal={ORGANIC LETTERS}, author={Comins, DL and Schilling, S and Zhang, YC}, year={2005}, month={Jan}, pages={95–98} }
 @article{comins_kuethe_miller_fevrier_brooks_2005, title={Diels-alder reactions of N-acyl-2-alkyl(aryl)-5-vinyl-2,3-dihydro-4-pyridones}, volume={70}, ISSN={["0022-3263"]}, DOI={10.1021/jo050559n}, abstractNote={Readily available N-acyl-5-vinyl-2,3-dihydro-4-pyridones undergo Diels-Alder cyclization with various dienophiles to afford novel octahydroquinolines containing synthetically useful functionality. With dihydropyridone 5 and cis-disubstituted dienophiles, the resulting cycloadducts were obtained as single diastereomers in good to excellent yield. The corresponding reaction of 5 with methyl acrylate, acrylonitrile, and phenyl vinyl sulfone showed modest preference for the endo adducts. The effect of the dihydropyridone C-2 and C-4 substituents on the degree of diastereofacial control was examined. By using this methodology, the core decahydroquinoline skeleton of gephyrotoxin was prepared in a stereocontrolled fashion. Interesting reactivity was observed with certain dienophiles leading to ring-opening of the initially formed cycloadducts. This tandem reaction provides a route to uniquely substituted beta-aminoketones, alcohols, and unnatural amino acids.}, number={13}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Comins, DL and Kuethe, JT and Miller, TM and Fevrier, FC and Brooks, CA}, year={2005}, month={Jun}, pages={5221–5234} }
 @article{fevrier_smith_comins_2005, title={Regioselective C-2 and C-6 substitution of (S)-nicotine and nicotine derivatives}, volume={7}, ISSN={["1523-7052"]}, DOI={10.1021/ol052196j}, abstractNote={[reaction: see text] Regioselective deprotonations of (S)-nicotine and derivatives at the C-2 and C-6 positions of the pyridine ring were performed in good to excellent yields. These methodologies allow the direct introduction of a plethora of functional groups onto the pyridine ring of nicotine.}, number={24}, journal={ORGANIC LETTERS}, author={Fevrier, FC and Smith, ED and Comins, DL}, year={2005}, month={Nov}, pages={5457–5460} }
 @article{comins_nolan_bori_2005, title={Regioselective lithium-halogen exchange and palladium-catalyzed cross-coupling reactions of 2,4-dihaloquinolines}, volume={46}, ISSN={["0040-4039"]}, DOI={10.1016/j.tetlet.2005.07.137}, abstractNote={Lithium–halogen exchange of 2,4-dibromoquinolines proceeds regioselectively at C-4 and affords 4-substituted quinolines on quenching with electrophiles. Palladium-catalyzed cross-coupling reactions of 2-bromo-4-iodoquinoline provide 4-substituted 2-bromoquinoline derivatives.}, number={39}, journal={TETRAHEDRON LETTERS}, author={Comins, DL and Nolan, JM and Bori, ID}, year={2005}, month={Sep}, pages={6697–6699} }
 @misc{comins_huang_2005, title={Short synthesis of pyridine-based pharmaceutical intermediates}, volume={6,855,825}, number={2005 Feb. 15}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Huang, S.-L.}, year={2005} }
 @article{comins_king_smith_fevrier_2005, title={Synthesis of C-4 substituted nicotine derivatives via an N-acylpyridinium salt of (S)-nicotine}, volume={7}, ISSN={["1523-7060"]}, DOI={10.1021/ol0520469}, abstractNote={[reaction: see text] A variety of novel nicotine derivatives were prepared from (S)-nicotine via a two-step sequence. Addition of a cuprate reagent to an N-acylpyridinium salt of nicotine, followed by aromatization with elemental sulfur, afforded C-4 substituted nicotines in moderate to high yield. Using this method, 4-(dimethylphenylsilyl)nicotine was prepared and oxidized to afford (S)-4-hydroxynicotine.}, number={22}, journal={ORGANIC LETTERS}, author={Comins, DL and King, LS and Smith, ED and Fevrier, FC}, year={2005}, month={Oct}, pages={5059–5062} }
 @article{young_comins_2005, title={Tandem directed lithiations of N-boc-1,2-dihydropyridines toward highly functionalized 2,3-dihydro-4-pyridones}, volume={7}, ISSN={["1523-7052"]}, DOI={10.1021/ol052313a}, abstractNote={[chemical reaction: see text]. Sequential tandem directed lithiations of an N-Boc-4-methoxy-1,2-dihydropyridine have been achieved, leading to C-5,C-6 disubstituted dihydropyridones on acidic workup. The chlorine atom of the dihydropyridone products can in turn be substituted giving rise to diverse substituents at C-6.}, number={25}, journal={ORGANIC LETTERS}, author={Young, DW and Comins, DL}, year={2005}, month={Dec}, pages={5661–5664} }
 @article{kuethe_comins_2004, title={Addition of indolyl and pyrrolyl grignard reagents to 1-acylpyridinium salts}, volume={69}, ISSN={["0022-3263"]}, DOI={10.1021/jo049943v}, abstractNote={Certain indolyl and pyrrolyl Grignard reagents add to 1-acyl salts of 4-methoxy-3-(triisopropylsilyl)pyridine to give the corresponding 1-acyl-2-heteroaryl-2,3-dihydro-4-pyridones in good to high yield. When the 1-acyl group contained a chiral auxiliary, (+/-)-trans-2-(alpha-cumyl)cyclohexyloxy, addition of the indolyl Grignards resulted in a separable mixture of diastereomeric 2,3-dihydro-4-pyridones.}, number={8}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Kuethe, JT and Comins, DL}, year={2004}, month={Apr}, pages={2863–2866} }
 @article{kuethe_comins_2004, title={Asymmetric total synthesis of (+)-cannabisativine}, volume={69}, ISSN={["0022-3263"]}, DOI={10.1021/jo049724+}, abstractNote={The asymmetric total synthesis of natural (+)-cannabisativine 1 was completed in 19 steps and 7% overall yield. The key synthetic intermediate 29 was prepared with a high degree of stereocontrol in 12 steps starting from chiral 1-acylpyridinium salt 10. Addition of zinc enolate 11 to pyridinium salt 10 furnished dihydropyridone 12 containing two contiguous stereocenters of the correct absolute configuration. Luche reduction of ketone 16 afforded diol 17 in high yield (96%) and excellent diastereoselectivity. The Mukaiyama-Michael reaction of pyridones 27a/b with O-silyl ketene acetal 32 gave phenyl selenyl ketones 33a/b with complete stereoselectivity. Elimination of cis-beta-hydroxyselenides 34 and 35 effected the regiocontrolled preparation of tetrahydropyridine derivative 29. Several approaches to the macrocyclic ring closure of the 13-membered ring were investigated, ultimately leading to the completion of an asymmetric synthesis of the target compound with a high degree of stereocontrol.}, number={16}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Kuethe, JT and Comins, DL}, year={2004}, month={Aug}, pages={5219–5231} }
 @article{gotchev_comins_2004, title={Novel heterocyclic systems. Synthesis of 2,7-dimethyl-10-oxa-1,8-diaza-anthracen-9-one and derivatives}, volume={60}, ISSN={["0040-4020"]}, DOI={10.1016/j.tet.2004.09.111}, abstractNote={Synthesis of novel heterocycles, which contain the unique 10-oxa-1,8-diazaanthracen-9-one tricyclic core, is reported. The core structure was assembled via a dehydrative-cyclization strategy.}, number={51}, journal={TETRAHEDRON}, author={Gotchev, DB and Comins, DL}, year={2004}, month={Dec}, pages={11751–11758} }
 @misc{fang_huie_xie_comins_2004, title={Preparation of a camptothecin derivative by intramolecular cyclisation}, volume={6,821,982}, number={2004 Nov. 23}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Fang, F. G. and Huie, E. M. and Xie, S. and Comins, D. L.}, year={2004} }
 @misc{comins_huang_2004, title={Short synthesis of pyridine-based pharmaceutical intermediates}, volume={6,706,884}, number={2004 Mar. 16}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Huang, S.-L.}, year={2004} }
 @article{kuethe_brooks_comins_2003, title={Diels-Alder reactions of 5-vinyl-1-acyl-2-aryl-2,3-dihydro-4-pyridones: regio- and stereoselective synthesis of octahydroquinolines}, volume={5}, ISSN={["1523-7052"]}, DOI={10.1021/ol027308a}, abstractNote={[reaction: see text] Readily available 5-vinyldihydropyridones 2 undergo Diels-Alder cyclization with various dienophiles to afford novel octahdroquinolines. The process is highly stereoselective and provides heterocyclic products containing synthetically useful functionality.}, number={3}, journal={ORGANIC LETTERS}, author={Kuethe, JT and Brooks, CA and Comins, DL}, year={2003}, month={Feb}, pages={321–323} }
 @misc{fang_huie_xie_comins_2003, title={Preparation of a camptothecin derivative by intramolecular cyclisation}, volume={6,559,309}, number={2003 May 6}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Fang, F. G. and Huie, E. M. and Xie, S.-P. and Comins, D. L.}, year={2003} }
 @article{nolan_comins_2003, title={Regioselective sonogashira couplings of 2,4-dibromoquinolines. A correction}, volume={68}, ISSN={["0022-3263"]}, DOI={10.1021/jo034122w}, abstractNote={Heteronuclear multiple bond correlation (HMBC) was used to determine the regiochemical outcome of palladium-catalyzed carbon-carbon bond formation between 2,4-dibromoquinolines and terminal acetylenes. The observed regioselectivity of these coupling reactions is opposite to that reported in the literature for analogous reactions.}, number={9}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Nolan, JM and Comins, DL}, year={2003}, month={May}, pages={3736–3738} }
 @misc{comins_huang_2003, title={Short synthesis of pyridine-based pharmaceutical intermediates}, volume={6,534,656}, number={2003 Mar. 18}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Huang, S.-L.}, year={2003} }
 @article{kuethe_comins_2003, title={Tandem Diels-Alder cyclization/aromatization reactions of 5-vinyl-1-acyl-2-aryl-2,3-dihydro-4-pyridones}, volume={44}, ISSN={["0040-4039"]}, DOI={10.1016/S0040-4039(03)00930-4}, abstractNote={A tandem Diels–Alder cyclization/aromatization of 5-vinyl-2,3-dihydro-4-pyridones and various dienophiles is reported. The intermediate Diels–Alder cycloadduct undergoes an elimination/aromatization to provide β-amino-ketones, β-amino-alcohols, and unnatural amino acids containing useful functionality.}, number={22}, journal={TETRAHEDRON LETTERS}, author={Kuethe, JT and Comins, DL}, year={2003}, month={May}, pages={4179–4182} }
 @article{williams_grillo_comins_2002, title={A novel free-radical ring contraction of a cyclic carbamate}, volume={67}, ISSN={["0022-3263"]}, DOI={10.1021/jo0163290}, abstractNote={During a study on iodocyclocarbamation reactions of 2-styryl-4-piperidones, a novel ring contraction was observed. Iodocyclocarbamation of 2-styryl-4-piperidone 3 gave the bicyclic carbamate 4. Reduction of 4 under free-radical conditions effected a stereoselective ring contraction to provide oxazolidinone 6. A three-electron-three-center mechanism is proposed.}, number={6}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Williams, AL and Grillo, TA and Comins, DL}, year={2002}, month={Mar}, pages={1972–1973} }
 @misc{fang_huie_xie_comins_2002, title={Preparation of a camptothecin derivative by intramolecular cyclisation}, volume={6,462,196}, number={2002 Oct. 8}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Fang, F. G. and Huie, E. M. and Xie, S. and Comins, D. L.}, year={2002} }
 @article{comins_killpack_despagnet_zeller_2002, title={Synthesis and reactions of enantiopure 1-acyl-2- [triaryl(alkyl)silyl]-2,3-dihydro-4-pyridones}, volume={58}, number={2002 Nov 22}, journal={Heterocycles}, author={Comins, D. L. and Killpack, M. O. and Despagnet, E. and Zeller, E.}, year={2002}, pages={505–519} }
 @article{joseph_comins_2002, title={Synthetic applications of chiral 2,3-dihydro-4-pyridones}, volume={5}, number={6}, journal={Current Opinion in Drug Discovery & Development}, author={Joseph, S. and Comins, D. L.}, year={2002}, pages={870–880} }
 @article{comins_zheng_goehring_2002, title={Total synthesis of the putative structure of the lupin alkaloid plumerinine}, volume={4}, ISSN={["1523-7052"]}, DOI={10.1021/ol025820q}, abstractNote={[reaction: see text]. A stereocontrolled synthesis of quinolizidine 1, the reported structure of plumerinine, has been accomplished in 10 steps from 4-methoxypyridine. The key step is a highly facial selective intramolecular [2 + 2] photocycloaddition of a 2,3-dihydro-4-pyridone. The reported spectral data for plumerinine did not match that of our synthetic 1.}, number={9}, journal={ORGANIC LETTERS}, author={Comins, DL and Zheng, XL and Goehring, RR}, year={2002}, month={May}, pages={1611–1613} }
 @article{comins_nolan_2001, title={A practical six-step synthesis of (S)-camptothecin}, volume={3}, ISSN={["1523-7060"]}, DOI={10.1021/ol0169271}, abstractNote={An asymmetric synthesis of (S)-camptothecin (1) has been accomplished in six steps starting from two commercially available heterocycles. [reaction: see text]}, number={26}, journal={ORGANIC LETTERS}, author={Comins, DL and Nolan, JM}, year={2001}, month={Dec}, pages={4255–4257} }
 @article{comins_sandelier_grillo_2001, title={Asymmetric synthesis of (+)-deoxoprosopinine}, volume={66}, DOI={10.1021/jo015834u}, abstractNote={ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTAsymmetric Synthesis of (+)-DeoxoprosopinineDaniel L. Comins, Matthew J. Sandelier, and Teresa Abad GrilloView Author Information Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204 [email protected]Cite this: J. Org. Chem. 2001, 66, 20, 6829–6832Publication Date (Web):September 6, 2001Publication History Received13 June 2001Published online6 September 2001Published inissue 1 October 2001https://doi.org/10.1021/jo015834uCopyright © 2001 American Chemical SocietyRequest reuse permissionsArticle Views843Altmetric-Citations44LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (53 KB) Get e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Cyclization,Enantioselective synthesis,Materials,Organic compounds,Pharmaceuticals Get e-Alerts}, number={20}, journal={Journal of Organic Chemistry}, author={Comins, D. L. and Sandelier, M. J. and Grillo, T. A.}, year={2001}, pages={6829–6832} }
 @article{comins_huang_mcardle_ingalls_2001, title={Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: A concise asymmetric synthesis of (+)-allopumiliotoxin 267A}, volume={3}, ISSN={["1523-7060"]}, DOI={10.1021/ol0069709}, abstractNote={A concise asymmetric synthesis of (+)-allopumiliotoxin 267A has been accomplished using an enantiopure dihydropyridone building block. The synthesis is highly stereoselective and requires 10 steps from readily available material.}, number={3}, journal={ORGANIC LETTERS}, author={Comins, DL and Huang, SL and McArdle, CL and Ingalls, CL}, year={2001}, month={Feb}, pages={469–471} }
 @article{comins_fulp_2001, title={Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: asymmetric synthesis of 1-deoxynojirimycin}, volume={42}, ISSN={["0040-4039"]}, DOI={10.1016/S0040-4039(01)01432-0}, abstractNote={An asymmetric synthesis of 1-deoxynojirimycin (2) mediated by a chiral auxiliary is reported. The dihydropyridone 4 was converted to diol 11 in three steps by acetoxylation, hydrolysis, and stereoselective reduction. Dihydroxylation of 11 followed by catalytic reduction afforded 2.}, number={39}, journal={TETRAHEDRON LETTERS}, author={Comins, DL and Fulp, AB}, year={2001}, month={Sep}, pages={6839–6841} }
 @article{comins_ollinger_2001, title={Inter- and intramolecular Horner-Wadsworth-Emmons reactions of 5-(diethoxyphosphoryl)-1-acyl-2-alkyl(aryl)-2,3-dihydro-4-pyridones}, volume={42}, ISSN={["0040-4039"]}, DOI={10.1016/S0040-4039(01)00690-6}, abstractNote={Dihydropyridones of the type 1 were converted to their C-5 alkylidene derivatives 2 by a reaction sequence involving phosphorylation, conjugate reduction or addition to provide piperidones 4, and then olefination via a Horner–Wadsworth–Emmons reaction. An intramolecular version of this method was used to prepare trans-bicyclic enone 13.}, number={25}, journal={TETRAHEDRON LETTERS}, author={Comins, DL and Ollinger, CG}, year={2001}, month={Jun}, pages={4115–4118} }
 @article{comins_williams_2001, title={Model studies toward the total synthesis of the Lycopodium alkaloid spirolucidine}, volume={3}, ISSN={["1523-7052"]}, DOI={10.1021/ol016556o}, abstractNote={[reaction: see text] A strategy for the synthesis of the spirocyclic core of spirolucidine was explored through a model study. The diene 4a was prepared and photolyzed to give the desired [2 + 2] photoadduct 17 containing the correct relative stereochemistry corresponding to spirolucidine.}, number={20}, journal={ORGANIC LETTERS}, author={Comins, DL and Williams, AL}, year={2001}, month={Oct}, pages={3217–3220} }
 @article{comins_brooks_ingalls_2001, title={Reduction of N-acyl-2,3-dihydro-4-pyridones to N-acyl-4-piperidones using zinc/acetic acid}, volume={66}, ISSN={["0022-3263"]}, DOI={10.1021/jo001609l}, abstractNote={ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTReduction of N-Acyl-2,3-dihydro-4-pyridones to N-Acyl-4-piperidones Using Zinc/Acetic AcidDaniel L. Comins, Clinton A. Brooks, and Charles L. IngallsView Author Information Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204 [email protected]Cite this: J. Org. Chem. 2001, 66, 6, 2181–2182Publication Date (Web):February 23, 2001Publication History Received13 November 2000Published online23 February 2001Published inissue 1 March 2001https://doi.org/10.1021/jo001609lCopyright © 2001 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views1185Altmetric-Citations23LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (26 KB) Get e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Catalytic reactions,Redox reactions,Transfer reactions,Zinc Get e-Alerts}, number={6}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Comins, DL and Brooks, CA and Ingalls, CL}, year={2001}, month={Mar}, pages={2181–2182} }
 @article{comins_hiebel_huang_2001, title={Synthesis and reactivity of N-acyl-5-(1-hydroxyalkyl)-2,3-dihydro-4-pyridones}, volume={3}, ISSN={["1523-7052"]}, DOI={10.1021/ol015529v}, abstractNote={[structure: see text]. The Nozaki-Hiyama-Kishi reaction was used to prepare the 5-(1-hydroxyalkyl)-2,3-dihydro-4-pyridones 3. Reduction, oxidation, and substitution reactions of 3 were examined.}, number={5}, journal={ORGANIC LETTERS}, author={Comins, DL and Hiebel, AC and Huang, SL}, year={2001}, month={Mar}, pages={769–771} }
 @article{kuethe_comins_2000, title={Addition of metallo enolates to chiral 1-acylpyridinium salts: Total synthesis of (+)-cannabisativine}, volume={2}, ISSN={["1523-7052"]}, DOI={10.1021/ol0056271}, abstractNote={[formula: see text] A novel route to the first asymmetric synthesis of (+)-cannabisativine (1) is described. The total synthesis of 1 was accomplished with a high degree of regio- and stereoselectivity in 19 steps and 9% overall yield.}, number={6}, journal={ORGANIC LETTERS}, author={Kuethe, JT and Comins, DL}, year={2000}, month={Mar}, pages={855–857} }
 @article{brooks_comins_2000, title={Asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid}, volume={41}, ISSN={["0040-4039"]}, DOI={10.1016/s0040-4039(00)00460-3}, abstractNote={An asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid was accomplished in eight steps and 31% overall yield.}, number={19}, journal={TETRAHEDRON LETTERS}, author={Brooks, CA and Comins, DL}, year={2000}, month={May}, pages={3551–3553} }
 @article{comins_williams_2000, title={Asymmetric synthesis of erythro- and threo-2-(1-hydroxyalkyl)piperidines via iodocyclocarbamation of 1-acyl-2-alkenyl-1,2,3,6-tetrahydropyridines}, volume={41}, ISSN={["0040-4039"]}, DOI={10.1016/S0040-4039(00)00298-7}, abstractNote={An iodocyclocarbamation procedure has been developed for the stereoselective preparation of erythro- and threo-2-(1-hydroxyalkyl)piperidines. This methodology was utilized in the asymmetric synthesis of two piperidine alkaloids, (+)-α-conhydrine and (+)-β-conhydrine.}, number={16}, journal={TETRAHEDRON LETTERS}, author={Comins, DL and Williams, AL}, year={2000}, month={Apr}, pages={2839–2842} }
 @misc{fang_huie_xie_comins_2000, title={Preparation of a camptothecin derivative by intramolecular cyclisation}, volume={6,063,923}, number={2000 May 16}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Fang, F. G. and Huie, E. M. and Xie, S.-P. and Comins, D. L.}, year={2000} }
 @article{huang_comins_2000, title={Total synthesis of (+)-streptazolin}, ISSN={["1359-7345"]}, DOI={10.1039/b001425g}, abstractNote={The first chiral auxiliary mediated asymmetric synthesis of 
(+)-streptazolin has been accomplished in 13 steps and with a high degree 
of stereocontrol.}, number={7}, journal={CHEMICAL COMMUNICATIONS}, author={Huang, SL and Comins, DL}, year={2000}, pages={569–570} }
 @article{comins_1999, title={Asymmetric synthesis and synthetic utility of 2,3-dihydro-4-pyridones}, volume={36}, ISSN={["1943-5193"]}, DOI={10.1002/jhet.5570360610}, abstractNote={Journal of Heterocyclic ChemistryVolume 36, Issue 6 p. 1491-1500 Article Asymmetric synthesis and synthetic utility of 2,3-dihydro-4-pyridones Daniel L. Comins, Daniel L. Comins Department of Chemistry, North Carolina State University, Raleigh, NC 27695–8204 USASearch for more papers by this author Daniel L. Comins, Daniel L. Comins Department of Chemistry, North Carolina State University, Raleigh, NC 27695–8204 USASearch for more papers by this author First published: 12 March 2009 https://doi.org/10.1002/jhet.5570360610Citations: 85AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Citing Literature Volume36, Issue6November/December 1999Pages 1491-1500 RelatedInformation}, number={6}, journal={JOURNAL OF HETEROCYCLIC CHEMISTRY}, author={Comins, DL}, year={1999}, pages={1491–1500} }
 @article{comins_green_1999, title={Asymmetric synthesis of dienomycin C}, volume={40}, ISSN={["0040-4039"]}, DOI={10.1016/S0040-4039(98)02273-4}, abstractNote={The first asymmetric synthesis of dienomycin C was accomplished in seven steps and 46% overall yield.}, number={2}, journal={TETRAHEDRON LETTERS}, author={Comins, DL and Green, GM}, year={1999}, month={Jan}, pages={217–218} }
 @misc{comins_libby_al-awar_foti_1999, title={Asymmetric synthesis of the Lycopodium alkaloid, N-a-acetyl-N-b-methylphlegmarine}, volume={64}, ISSN={["0022-3263"]}, DOI={10.1021/jo990192k}, abstractNote={ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTAsymmetric Synthesis of the Lycopodium Alkaloid, Na-Acetyl-Nb-methylphlegmarineDaniel L. Comins, Adam H. Libby, Rima S. Al-awar, and Christopher J. FotiView Author Information Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204 Cite this: J. Org. Chem. 1999, 64, 7, 2184–2185Publication Date (Web):March 6, 1999Publication History Received2 February 1999Published online6 March 1999Published inissue 1 April 1999https://doi.org/10.1021/jo990192kCopyright © 1999 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views1204Altmetric-Citations59LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (151 KB) Get e-AlertsSupporting Info (2)»Supporting Information Supporting Information SUBJECTS:Enantioselective synthesis,Hydrocarbons,Organic compounds,Redox reactions,Stereochemistry Get e-Alerts}, number={7}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Comins, DL and Libby, AH and Al-awar, RS and Foti, CJ}, year={1999}, month={Apr}, pages={2184–2185} }
 @article{comins_kuethe_hong_lakner_concolino_rheingold_1999, title={Diastereoselective addition of prochiral metallo enolates to chiral 1-acylpyridinium salts}, volume={121}, ISSN={["0002-7863"]}, DOI={10.1021/ja990024+}, number={11}, journal={JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, author={Comins, DL and Kuethe, JT and Hong, H and Lakner, FJ and Concolino, TE and Rheingold, AL}, year={1999}, month={Mar}, pages={2651–2652} }
 @article{comins_fulp_1999, title={Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric synthesis of (-)-slaframine}, volume={1}, ISSN={["1523-7060"]}, DOI={10.1021/ol991083v}, abstractNote={[formula: see text] An asymmetric synthesis of (-)-slaframine and N-acetylslaframine has been accomplished starting from an enantiopure dihydropyridone building block. The oxygen-carbon bond at C-1 was incorporated with complete stereoselectivity by using an efficient phenylselenocyclocarbamation reaction.}, number={12}, journal={ORGANIC LETTERS}, author={Comins, DL and Fulp, AB}, year={1999}, month={Dec}, pages={1941–1943} }
 @article{comins_zhang_joseph_1999, title={Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric synthesis of benzomorphans}, volume={1}, ISSN={["1523-7060"]}, DOI={10.1021/ol990738p}, abstractNote={[formula: see text] Concise asymmetric syntheses of several benzomorphan derivatives have been accomplished using enantiopure 2,3-dihydro-4-pyridones as chiral building blocks.}, number={4}, journal={ORGANIC LETTERS}, author={Comins, DL and Zhang, YM and Joseph, SP}, year={1999}, month={Aug}, pages={657–659} }
 @article{comins_brooks_al-awar_goehring_1999, title={IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids: Asymmetric synthesis of (+)-luciduline}, volume={1}, ISSN={["1523-7060"]}, DOI={10.1021/ol990028j}, abstractNote={[formula: see text] The first chiral auxiliary mediated asymmetric synthesis of the naturally occurring Lycopodium alkaloid (+)-luciduline has been accomplished. Key steps include an IMDA reaction of a chiral dihydropyridine, a subsequent retro-Mannich ring opening, and a novel cationic reductive cyclization reaction.}, number={2}, journal={ORGANIC LETTERS}, author={Comins, DL and Brooks, CA and Al-awar, RS and Goehring, RR}, year={1999}, month={Jul}, pages={229–231} }
 @article{kuethe_comins_1999, title={The Mukaiyama-Michael reaction of N-acyl-2,3-dihydro-4- pyridones: Regio- and stereoselective synthesis of cis-2,6- disubstituted 1,2,5,6-tetrahydropyridines}, volume={1}, DOI={10.1021/ol9908124}, abstractNote={[formula: see text] A convenient regio- and stereoselective preparation of 1,2,5,6-tetrahydropyridines of the type 1 has been developed, starting from readily available N-acyl-2,3-dihydro-4-pyridones 2.}, number={7}, journal={Organic Letters}, author={Kuethe, J. T. and Comins, D. L.}, year={1999}, pages={1031–1033} }
 @article{comins_stolze_thakker_mcardle_1998, title={C-3 acetoxylation of N-acyl-2,3-dihydro-4-pyridones}, volume={39}, ISSN={["0040-4039"]}, DOI={10.1016/S0040-4039(98)01195-2}, abstractNote={Stereoselective acetoxylation at the C-3 position of N-acyl-2-alkyl-2,3-dihydro-4-pyridones was effected with Pb(OAc)4in refluxing toluene.}, number={32}, journal={TETRAHEDRON LETTERS}, author={Comins, DL and Stolze, DA and Thakker, P and McArdle, CL}, year={1998}, month={Aug}, pages={5693–5696} }
 @article{comins_lee_boyle_1998, title={Intramolecular photocycloaddition of a tethered bis-2,3-dihydro-4-pyridone: Stereochemistry and reactivity of the cycloadduct}, volume={39}, ISSN={["0040-4039"]}, DOI={10.1016/S0040-4039(97)10520-2}, abstractNote={Abstract The photocycloaddition of enantiopure bis-dihydropyridone 4 provided a single cycloadduct in high yield. Treatment of the cycloadduct with SmI2 effected ring opening and intramolecular aldol addition to give pentacyclic β-hydroxyketone 7.}, number={3-4}, journal={TETRAHEDRON LETTERS}, author={Comins, DL and Lee, YS and Boyle, PD}, year={1998}, month={Jan}, pages={187–190} }
 @article{comins_foti_libby_1998, title={Model studies toward the synthesis of N alpha-acetyl-N beta- methylphlegmarine: Addition of cyclohexylmethyl organometallics to 1-acylpyridinium salts}, volume={48}, DOI={10.3987/com-98-8148}, number={7}, journal={Heterocycles}, author={Comins, D. L. and Foti, C. J. and Libby, A. H.}, year={1998}, pages={1313–1317} }
 @article{comins_zhang_zheng_1998, title={Photochemical reactions of chiral 2,3-dihydro-4(1H)-pyridones: asymmetric synthesis of (-)-perhydrohistrionicotoxin}, ISSN={["1359-7345"]}, DOI={10.1039/a807448h}, abstractNote={The first chiral auxiliary-mediated asymmetric synthesis of (–)-perhydrohistrionicotoxin is described.}, number={22}, journal={CHEMICAL COMMUNICATIONS}, author={Comins, DL and Zhang, YM and Zheng, XL}, year={1998}, month={Nov}, pages={2509–2510} }
 @article{comins_joseph_hong_alawar_foti_zhang_chen_lamunyon_guerraweltzien_1997, title={Asymmetric synthesis and synthetic utility of 2,3-dihydro-4-pyridones}, volume={69}, ISSN={["0033-4545"]}, DOI={10.1351/pac199769030477}, abstractNote={Abstract}, number={3}, journal={PURE AND APPLIED CHEMISTRY}, author={Comins, DL and Joseph, SP and Hong, H and Alawar, RS and Foti, CJ and Zhang, YM and Chen, XH and LaMunyon, DH and GuerraWeltzien, M}, year={1997}, month={Mar}, pages={477–481} }
 @article{comins_thakker_baevsky_badawi_1997, title={Chiral auxiliary mediated Pictet-Spengler reactions - Asymmetric syntheses of (-)-laudanosine, (+)-glaucine and (-)-xylopinine.}, volume={53}, ISSN={["0040-4020"]}, DOI={10.1016/S0040-4020(97)01018-1}, abstractNote={Cyclohexyl-based chiral auxiliaries can be used effectively in an asymmetric Pictet-Spengler synthesis of tetrahydroisoquinoline, aporphine and protoberbine alkaloids. Using this strategy, concise asymmetric syntheses of (−)-laudanosine, (+)-glaucine and (+)-xylopinine have been accomplished.}, number={48}, journal={TETRAHEDRON}, author={Comins, DL and Thakker, PM and Baevsky, MF and Badawi, MM}, year={1997}, month={Dec}, pages={16327–16340} }
 @article{comins_lamunyon_chen_1997, title={Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric syntheses of indolizidine alkaloids (-)-205A, (-)-207A, and (-)-235B}, volume={62}, ISSN={["0022-3263"]}, DOI={10.1021/jo971448u}, abstractNote={Concise asymmetric syntheses of indolizidine alkaloids (-)-205A, (-)-207A, and (-)-235B were accomplished with a high degree of stereocontrol in eleven steps. Addition of 4-(1-butenyl)magnesium bromide to 1-acylpyridinium salt 5, prepared in situ from 4-methoxy-3-(triisopropylsilyl)pyridine and the chloroformate of (+)-trans-2-(alpha-cumyl)cyclohexanol, gave a 91% yield of diastereomerically pure dihydropyridone 6. Oxidative cleavage of 6 and subsequent reduction provided alcohol 7 in 81% yield. Removal of the chiral auxilliary and TIPS group (NaOMe; 10% HCl), N-acylation with BnOCOCCl, and treatment with NCS/Ph(3)P gave chloride 10. Methylation at C-3, copper-mediated conjugate addition of 4-(benzyloxy)butylmagnesium bromide, and vinyl triflate formation provided 13 in a stereoselective fashion. Catalytic reduction of the vinyl triflate moiety, simultaneous cleavage of the benzyl ether and Cbz groups, and cyclization to give amino alcohol 14 was effected via a one-pot reaction. Oxidation of 14 with the Dess-Martin reagent gave a 97% yield of amino aldehyde 4. Synthesis of each of the three title alkaloids was accomplished in one step from 4. The Seyferth-Gilbert reaction provided a 41% yield of (-)-205A. The appropriate Wittig olefination of 4 gave indolizidines (-)-207A and (-)-235B in 70% and 86% yield, respectively.}, number={23}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Comins, DL and LaMunyon, DH and Chen, XH}, year={1997}, month={Nov}, pages={8182–8187} }
 @article{comins_chen_morgan_1997, title={Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric synthesis of (-)-septicine and (-)-tylophorine}, volume={62}, ISSN={["0022-3263"]}, DOI={10.1021/jo9711495}, abstractNote={A concise asymmetric synthesis of (-)-septicine (1) and (-)-tylophorine (2) was accomplished with a high degree of stereocontrol in eight and nine steps, respectively. Addition of 4-(1-butenyl)magnesium bromide to 1-acylpyridinium salt 3, prepared in situ from 4-methoxy-3-(triisopropylsilyl)pyridine and the chloroformate of (-)-trans-2-(alpha-cumyl)cyclohexanol, gave a 91% yield of diastereomerically pure dihydropyridone 7. Oxidative cleavage of 7 and subsequent reduction provided alcohol 6 in 81% yield. Conversion of 6 to the chloride followed by treatment with sodium methoxide gave indolizidinone 9 in high yield. Bromination and conjugate reduction of 9 with L-Selectride, and trapping the intermediate enolate with N-(5-chloro-2-pyridyl)triflimide, provided bromovinyl triflate 11. Palladium-catalyzed cross-coupling of excess (3,4-dimethoxyphenyl)zinc bromide and 11 gave (-)-septicine (1). On the basis of this synthesis, (-)-1 was assigned the Rconfiguration. Reaction of 1 with vanadium(V) trifluoride oxide in TFA/CH(2)Cl(2) effected oxidative coupling to give a 68% yield of (-)-tylophorine (2).}, number={21}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Comins, DL and Chen, XH and Morgan, LA}, year={1997}, month={Oct}, pages={7435–7438} }
 @misc{comins_1996, title={Method of making asymmetric DE ring intermediates for the synthesis of camptothecin analogs}, volume={5,486,615}, number={1996 Jan. 23}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L.}, year={1996} }
 @misc{comins_1996, title={Method of making asymmetric DE ring intermediates for the synthesis of camptothecin and camptothecin analogs}, volume={5,496,952}, number={1996 Mar. 5}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L.}, year={1996} }
 @misc{comins_1995, title={14-halo-camptothecins}, volume={5,459,269}, number={1995 Oct. 17}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L.}, year={1995} }
 @misc{comins_baevsky_1995, title={Camptothecin intermediates and method of making camptothecin and comptothecin analogs}, volume={5,475,108}, number={1995 Dec. 12}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baevsky, M. F.}, year={1995} }
 @misc{comins_1995, title={Method of making asymmetric de ring intermediates for the synthesis of camptothecin and camptothecin analogs}, volume={5,395,939}, number={1995 Mar. 7}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L.}, year={1995} }
 @misc{comins_baevsky_1995, title={Method of making intermediates for camptothecin and its analogs}, volume={5,478,943}, number={1995 Dec. 26}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baevsky, M. F.}, year={1995} }
 @misc{comins_baesky_1994, title={Process for making DE ring intermediates for the synthesis of camptothecin and camptothecin analogs}, volume={5,315,007}, number={1994 May 2}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baesky, M. F.}, year={1994} }
 @misc{comins_baevsky_1994, title={Pyridinecarboxaldehyde D-ring intermediates useful for the synthesis of camptothecin and camptothecin analogs}, volume={5,321,140}, number={1994 Jun. 14}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baevsky, M. F.}, year={1994} }
 @misc{comins_baesky_1993, title={Alkoxymethylpyridine d-ring intermediates useful for the synthesis of camptpthecin and camptothecin analogs}, volume={5,254,690}, number={1993 Oct. 19}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baesky, M. F.}, year={1993} }
 @misc{comins_baesky_1993, title={Alkylpyridone DE ring intermediates useful for the manufacture of camptothecin and camptothecin analogs}, volume={5,243,050}, number={1993 Sep. 7}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baesky, M. F.}, year={1993} }
 @misc{comins_baesky_1993, title={Camptothecin intermediate and method of making camptothecin intermediates}, volume={5,191,082}, number={1993 Mar. 2}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baesky, M. F.}, year={1993} }
 @misc{comins_baesky_1993, title={Camptothecin intermediates and method of making same}, volume={5,200,524}, number={1993 Apr. 6}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baesky, M. F.}, year={1993} }
 @misc{comins_salvador_1993, title={Cycloalkyl-based chiral auxiliaries and method making the same}, volume={5,262,571}, number={1993 Nov. 26}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Salvador, J. M.}, year={1993} }
 @misc{comins_baevsky_1993, title={D ring intermediates for the synthesis of camptothecin and camptothecin analogs}, volume={5,264,579}, number={1993  Nov. 23}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baevsky, M. F.}, year={1993} }
 @misc{comins_baesky_1993, title={Method of making intermediates useful for the manufacture of camptothecin and camptothecin analogs}, volume={5,247,089}, number={1993 Sep. 21}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baesky, M. F.}, year={1993} }
 @misc{comins_baesky_1993, title={Methods and intermediates for the assymmetric synthesis of camptothecin and camptothecin analogs}, volume={5,212,317}, number={1993 May 18}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baesky, M. F.}, year={1993} }
 @misc{comins_baesky_1993, title={Optically pure D,E ring intermediates useful for the synthesis of camptothecin and camptothecin analogs}, volume={5,258,516}, number={1993 Nov. 2}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baesky, M. F.}, year={1993} }
 @misc{comins_baesky_1992, title={Intermediates and method of making camptothecin and camptothecin analogs}, volume={5,162,532}, number={1992 Nov. 10}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Baesky, M. F.}, year={1992} }
 @article{comins_dehghani_1992, title={PYRIDINE-DERIVED TRIFLATING REAGENTS - AN IMPROVED PREPARATION OF VINYL TRIFLATES FROM METALLO ENOLATES}, volume={33}, ISSN={["0040-4039"]}, DOI={10.1016/S0040-4039(00)60957-7}, abstractNote={Metallo enolates of ketones are trapped with an N-(2-pyridyl)triflimide at low temperatures to give vinyl triflates.}, number={42}, journal={TETRAHEDRON LETTERS}, author={COMINS, DL and DEHGHANI, A}, year={1992}, month={Oct}, pages={6299–6302} }