Daniel L. Comins

Works (123)

Updated: August 16th, 2024 13:38

2022 journal article

Synthesis of MAPA Reagents and 2-Alkyl(aryl)aminopyridines from 2-Bromopyridine Using the Goldberg Reaction

MOLECULES, 27(6).

By: D. Comins n

author keywords: N-methyl-N-(2-pyridyl)formamide; 2-methylaminopyridine amides; 2-alkyl(aryl)aminopyridines; Goldberg reaction; copper-catalyzed reactions; cross-coupling reactions; 1; 10-phenanthroline
MeSH headings : Amides; Aminopyridines; Catalysis; Hydrolysis; Indicators and Reagents
Source: Web Of Science
Added: April 11, 2022

2021 journal article

Preparation of substituted alkoxypyridines via directed metalation and metal-halogen exchange

ARKIVOC, 57–72.

By: I. Bori n & D. Comins n

author keywords: Alkoxypyridines; directed metalation; metal-halogen exchange; halogen dance reactions
Source: Web Of Science
Added: June 21, 2021

2016 article

Editorial for the Special Issue on Heterocycles

Comins, D., & Ma, D. (2016, November 4). JOURNAL OF ORGANIC CHEMISTRY, Vol. 81, pp. 10107–10108.

By: D. Comins n & D. Ma*

Source: Web Of Science
Added: August 6, 2018

2016 journal article

Studies toward the Synthesis of Lepadiformine A

JOURNAL OF ORGANIC CHEMISTRY, 81(21), 10433–10443.

By: S. Tsukanov n, L. Marks n & D. Comins n

MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Animals; Carbon-13 Magnetic Resonance Spectroscopy; Cyclization; Molecular Structure; Proton Magnetic Resonance Spectroscopy; Stereoisomerism; Urochordata / chemistry
TL;DR: An original approach to access a tricyclic framework of the lepadiformine-type alkaloids using a Grignard/N-acylpyridinium salt reaction to establish the desired absolute stereochemistry at the C2 position of the target alkaloid. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2016 journal article

Synthesis of C-4 Substituted Amido Nicotine Derivatives via Copper(I)- and (II)-Catalyzed Cross-Coupling Reactions

JOURNAL OF ORGANIC CHEMISTRY, 81(22), 11529–11534.

By: J. Zhu n, M. Enamorado n & D. Comins n

MeSH headings : Amides / chemistry; Carbon-13 Magnetic Resonance Spectroscopy; Catalysis; Copper / chemistry; Mass Spectrometry; Nicotine / chemical synthesis; Nicotine / chemistry; Proton Magnetic Resonance Spectroscopy
TL;DR: The syntheses of seven novel amido nicotine derivatives 12-18 from (S)-nicotine are presented, providing a useful method for preparing C-4 amide-containing nicotine analogs. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

2015 journal article

A concise synthesis of the Lycopodium alkaloid cermizine D

TETRAHEDRON LETTERS, 56(23), 3683–3685.

By: M. Enamorado n, C. Connelly n, A. Deiters n & D. Comins n

author keywords: Alkaloid synthesis; Lycopodium alkaloids; Nitrogen heterocycles; 1-Acylpyridinium salts; Asymmetric synthesis
Source: Web Of Science
Added: August 6, 2018

2015 journal article

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

TETRAHEDRON, 71(39), 7354–7360.

By: A. Hiebel n & D. Comins n

author keywords: Alkaloid synthesis; Nitrogen heterocycles; 1-Acylpyridinium salts; Asymmetric synthesis
Source: Web Of Science
Added: August 6, 2018

2014 journal article

A Twist on Facial Selectivity of Hydride Reductions of Cyclic Ketones: Twist-Boat Conformers in Cyclohexanone, Piperidone, and Tropinone Reactions

JOURNAL OF ORGANIC CHEMISTRY, 79(23), 11609–11618.

MeSH headings : Borohydrides / chemistry; Catalysis; Cyclohexanones / chemistry; Ketones / chemistry; Lithium Compounds / chemistry; Molecular Conformation; Molecular Structure; Piperidones / chemistry; Stereoisomerism; Tropanes / chemistry
TL;DR: It is 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 smallhydride reagent (LiAlH4) but not with a bulky hyDRide (lithium triisopropylborohydride). (via Semantic Scholar)
UN Sustainable Development Goal Categories
14. Life Below Water (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

2014 journal article

Studies toward the Total Synthesis of Dihydrolycolucine. Preparation of AB and CEF Ring Fragments

JOURNAL OF ORGANIC CHEMISTRY, 79(12), 5740–5745.

By: B. Cash n, N. Prevost n, F. Wagner & D. Comins n

MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Lycopodium / chemistry; Molecular Structure; Pyridinium Compounds / chemistry; Quinolines / chemical synthesis; Quinolines / chemistry; Stereoisomerism
TL;DR: A strategy for the synthesis of the lycopodium alkaloid dihydrolycolucine was investigated and key reactions include IMDA cycloadditions and retro-Mannich ring-openings to form both the AB and the EF ring fragments. (via Semantic Scholar)
Source: Web Of Science
Added: August 6, 2018

2014 journal article

Total Synthesis of Alkaloid 205B

JOURNAL OF ORGANIC CHEMISTRY, 79(19), 9074–9085.

By: S. Tsukanov n & D. Comins n

MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Catalysis; Heterocyclic Compounds, 3-Ring / chemical synthesis; Heterocyclic Compounds, 3-Ring / chemistry; Molecular Structure; Pyridines / chemical synthesis; Pyridines / chemistry; Stereoisomerism
TL;DR: 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. (via Semantic Scholar)
Source: Web Of Science
Added: August 6, 2018

2013 review

Dihydropyridine preparation and application in the synthesis of pyridine derivatives

[Review of ]. Advances in heterocyclic chemistry, vol 110, 110, 175–235.

By: D. Comins, K. Higuchi & D. Young

Source: NC State University Libraries
Added: August 6, 2018

2012 journal article

Studies toward the synthesis of spirolucidine. Preparation of ABC and EF ring fragments

TETRAHEDRON LETTERS, 53(11), 1347–1350.

By: J. Sahn n, P. Bharathi n & D. Comins n

author keywords: Alkaloid synthesis; Lycopodium alkaloids; Nitrogen heterocycles; 1-Acylpyridinium salts; Asymmetric synthesis
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2011 journal article

Concise Total Synthesis of the Frog Alkaloid (-)-205B

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 50(37), 8626–8628.

By: S. Tsukanov n & D. Comins*

author keywords: alkaloids; dihydropyridones; natural products; total synthesis; Tsuji-Trost reaction
MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Animals; Anura; Heterocyclic Compounds, 3-Ring / chemical synthesis; Heterocyclic Compounds, 3-Ring / chemistry; Molecular Conformation; Stereoisomerism
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2011 journal article

Hydrophobic Derivatization of N-linked Glycans for Increased Ion Abundance in Electrospray Ionization Mass Spectrometry

JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 22(8), 1309–1317.

By: S. Walker n, L. Lilley*, M. Enamorado n, D. Comins n & D. Muddiman n

author keywords: Hydrophobic Derivatization; HILIC; nanoESI; N-Linked Glycans; Hydrazone Formation
MeSH headings : Blood Proteins / chemistry; Carbohydrate Sequence; Chromatography, Liquid; Glycoproteins / chemistry; Humans; Hydrazines / chemistry; Hydrophobic and Hydrophilic Interactions; Polysaccharides / chemistry; Small Molecule Libraries; Spectrometry, Mass, Electrospray Ionization / methods; Tandem Mass Spectrometry
TL;DR: 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 gly can derivatization. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, NC State University Libraries
Added: August 6, 2018

2011 journal article

Identification and replication of loci involved in camptothecin-induced cytotoxicity using CEPH pedigrees

PLoS One, 6(5).

By: V. Watson, A. Motsinger-Reif, N. Hardison, E. Peters, T. Havener, L. Everitt, J. Auman, D. Comins, H. McLeod

Source: NC State University Libraries
Added: August 6, 2018

2010 journal article

A Five-Step Synthesis of (S)-Macrostomine from (S)-Nicotine

ORGANIC LETTERS, 12(20), 4513–4515.

By: M. Enamorado n, P. Ondachi n & D. Comins n

MeSH headings : Isoquinolines / chemical synthesis; Molecular Structure; Nicotine / chemistry
TL;DR: 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. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2010 journal article

Asymmetric Synthesis of All the Known Phlegmarine Alkaloids

JOURNAL OF ORGANIC CHEMISTRY, 75(24), 8564–8570.

By: B. Wolfe n, A. Libby n, R. Al-awar n, C. Foti n & D. Comins n

MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Indicators and Reagents / chemistry; Magnetic Resonance Spectroscopy; Molecular Conformation; Molecular Structure; Stereoisomerism
TL;DR: 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. (via Semantic Scholar)
Source: Web Of Science
Added: August 6, 2018

2010 journal article

Improving limits of detection for B-type natriuretic peptide using PC-IDMS: An application of the ALiPHAT strategy

ANALYST, 135(1), 36–41.

By: C. Shuford n, D. Comins n, J. Whitten n, J. Burnett* & D. Muddiman n

MeSH headings : Alkylating Agents / chemistry; Hydrophobic and Hydrophilic Interactions; Iodoacetamide / chemistry; Isotope Labeling; Limit of Detection; Natriuretic Peptide, Brain / analysis; Spectrometry, Mass, Electrospray Ionization / methods; Trypsin / metabolism
TL;DR: Evaluated alkylation reagents for their utility in quantifying B-type Natriuretic Peptide, a low abundance cardiac biomarker, by protein cleavage isotope dilution mass spectrometry found a approximately 3.5-fold decrease in the detection limit for the best performing hydrophobic reagent, 2-iodo-N-octylacetamide. (via Semantic Scholar)
Sources: Web Of Science, NC State University Libraries
Added: August 6, 2018

2010 journal article

Increasing the hydrophobicity and electrospray response of glycans through derivatization with novel cationic hydrazides

CHEMICAL COMMUNICATIONS, 46(2), 237–239.

By: M. Bereman n, D. Comins n & D. Muddiman n

TL;DR: 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. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, NC State University Libraries
Added: August 6, 2018

2010 article

Interplay of Permanent Charge and Hydrophobicity in the Electrospray Ionization of Glycans

Walker, S. H., Papas, B. N., Comins, D. L., & Muddiman, D. C. (2010, August 1). ANALYTICAL CHEMISTRY, Vol. 82, pp. 6636–6642.

By: S. Walker n, B. Papas n, D. Comins n & D. Muddiman n

TL;DR: The effectiveness of the incorporation of a permanent charge is studied and determined to hamper glycan analysis and 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). (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, NC State University Libraries
Added: August 6, 2018

2010 patent

Regiospecific synthesis of nicotine derivatives

By: L. King, E. Smith & D. Comins

Source: NC State University Libraries
Added: August 6, 2018

2010 journal article

Synthesis of Fused-Ring Nicotine Derivatives from (S)-Nicotine

JOURNAL OF ORGANIC CHEMISTRY, 75(5), 1706–1716.

By: P. Ondachi n & D. Comins n

MeSH headings : Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis; Bridged Bicyclo Compounds, Heterocyclic / chemistry; Cyclization; Dioxins / chemical synthesis; Dioxins / chemistry; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Nicotine / chemical synthesis; Nicotine / chemistry; Stereoisomerism
TL;DR: The synthesis of novel fused-ring bicyclic and tricyclic nicotine derivatives from natural (S)-nicotine are described and attempts to synthesize furonicotines resulted in formation of the furonicotine dimers 42 and 49. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2010 journal article

[2+2] Photochemical Cycloaddition/Ring Opening of 6-Alkenyl-2,3-dihydro-4-pyridones

JOURNAL OF ORGANIC CHEMISTRY, 75(19), 6728–6731.

By: J. Sahn n & D. Comins n

MeSH headings : Cyclization; Molecular Structure; Photochemistry; Pyridones / chemical synthesis; Pyridones / chemistry; Stereoisomerism
TL;DR: 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. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

2009 journal article

Chiral amino alcohols derived from (S)-6-chloronicotine as catalysts for asymmetric synthesis

TETRAHEDRON LETTERS, 50(16), 1806–1808.

By: S. Capracotta n & D. Comins n

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2009 journal article

Evaluation of the ALiPHAT Method for PC-IDMS and Correlation of Limits-of-Detection with Nonpolar Surface Area

JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 20(11), 2006–2012.

By: D. Williams n, D. Comins n, J. Whitten n & D. Muddiman n

MeSH headings : Alkylation; Amino Acid Sequence; Calibration; Carbon Isotopes / chemistry; Chromatography, High Pressure Liquid / methods; Humans; Hydrophobic and Hydrophilic Interactions; Isotope Labeling / methods; Laminin / analysis; Laminin / chemistry; Male; Mass Spectrometry / methods; Nitrogen Isotopes / chemistry; Oligopeptides / analysis; Oligopeptides / chemistry; Prostate-Specific Antigen / chemistry; Reference Standards; Trypsin / analysis; Trypsin / chemistry
TL;DR: While an increase in hydrophobicity was found to aid in decreasing LOD to an extent, beyond a certain hydrophOBicity, the number of decreases in LOD was observed, the authors observed a decrease. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, NC State University Libraries
Added: August 6, 2018

2009 journal article

Synthesis of 1,3-Amino Alcohol Derivatives via a Silicon-Mediated Ring-Opening of Substituted Piperidines

ORGANIC LETTERS, 11(13), 2940–2942.

By: W. McCall n & D. Comins n

MeSH headings : Amino Alcohols / chemical synthesis; Amino Alcohols / chemistry; Cyanogen Bromide / chemistry; Molecular Structure; Piperidines / chemistry; Stereoisomerism; Trimethylsilyl Compounds / chemistry
TL;DR: Multisubstituted piperidines containing a trimethylsilylmethyl group at C-2 can be opened regioselectively with TBAF and cyanogen bromide for stereoselective synthesis of alkylamine derivatives containing multiple chiral centers. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2009 patent

Synthesis of nicotine derivatives from nicotine

By: D. Comins & E. Smith

Source: NC State University Libraries
Added: August 6, 2018

2008 journal article

Identification of cuticular lipids eliciting interspecific courtship in the German cockroach, Blattella germanica

NATURWISSENSCHAFTEN, 95(5), 403–412.

By: D. Eliyahu n, S. Nojima n, S. Capracotta n, D. Comins n & C. Schal n

Contributors: D. Eliyahu n, S. Nojima n, S. Capracotta n, D. Comins n & C. Schal n

author keywords: Blatta orientalis; contact pheromone; methyl ketone; 11-methylheptacosan-2-one; 27-oxo-11-methylheptacosan-2-one
MeSH headings : Animals; Blattellidae / physiology; Female; Germany; Male; Pheromones / physiology; Reproduction; Sexual Behavior, Animal / physiology
TL;DR: It is proposed 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. (via Semantic Scholar)
UN Sustainable Development Goal Categories
15. Life on Land (Web of Science)
Sources: Web Of Science, ORCID, NC State University Libraries
Added: August 6, 2018

2008 journal article

N-Acyldihydropyridones as Synthetic Intermediates. A Stereoselective Synthesis of Acyclic Amino Alcohols Containing Multiple Chiral Centers

JOURNAL OF ORGANIC CHEMISTRY, 73(24), 9744–9751.

By: W. McCall n, T. Grillo n & D. Comins n

MeSH headings : Amino Alcohols / chemical synthesis; Amino Alcohols / chemistry; Catalysis; Cyanogen Bromide / chemistry; Hydrogenation; Indicators and Reagents; Magnetic Resonance Spectroscopy; Mass Spectrometry; Models, Molecular; Molecular Conformation; Piperidines / chemistry; Spectrophotometry, Infrared; Stereoisomerism
TL;DR: Various multisubstituted piperidines containing a phenyl group at C-2 can be opened regio- and stereoselectively with cyanogen bromide to create uniquely substituted alkylamine derivatives containing multiple chiral centers and various functionality. (via Semantic Scholar)
Source: Web Of Science
Added: August 6, 2018

2008 journal article

Stereoselective synthesis of acyclic amino alcohols via von Braun ring opening of chiral piperidines

ORGANIC LETTERS, 10(15), 3255–3257.

By: W. McCall n, T. Grillo n & D. Comins n

MeSH headings : Amino Alcohols / chemical synthesis; Benzyl Compounds / chemistry; Cyanamide / chemistry; Cyanogen Bromide / chemistry; Cyclization; Piperidines / chemistry; Stereoisomerism
TL;DR: Multisubstituted piperidines containing a phenyl group at C-2 can be opened regio- and stereoselectively with cyanogen bromide and contain useful cyanamide and benzylic bromides functional groups. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2008 journal article

Synthesis and regioselective substitution of C-6 alkoxy derivatives of (S)-nicotine

TETRAHEDRON LETTERS, 49(3), 569–572.

By: P. Ondachi n & D. Comins n

author keywords: (S)-nicotine; alkoxynicotine; lithiation; regioselective deprotonation
TL;DR: Enantiopure (S)-6-alkoxynicotine derivatives have been synthesized in two steps from (S-nicotine via (S)"6-iodonicotine", using mesityllithium as the base at 0 °C fordeprotonation and substitution at the C-5 position of the pyridine ring of (S)+6-methoxynICotine. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2008 patent

Synthesis of nicotine derivatives from nicotine

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & S. D.

Source: NC State University Libraries
Added: August 6, 2018

2008 journal article

Synthesis, characterization, and application of lodoacetamide derivatives utilized for the ALiPHAT strategy

Journal of the American Chemical Society, 130(7), 2122-.

By: D. Williams, C. Meadows, I. Bori, A. Hawkridge, D. Comins & D. Muddiman

Sources: NC State University Libraries, NC State University Libraries
Added: August 6, 2018

2007 journal article

Achieving augmented limits of detection for peptides with hydrophobic alkyl tags

ANALYTICAL CHEMISTRY, 79(11), 3989–3995.

By: J. Frahm n, I. Bori n, D. Comins n, A. Hawkridge n & D. Muddiman n

MeSH headings : Acetates / chemistry; Alkylation; Amides / chemical synthesis; Amides / chemistry; Amino Acid Sequence; Chlorides / chemistry; Hydrophobic and Hydrophilic Interactions; Iodine / chemistry; Molecular Sequence Data; Peptides / analysis; Peptides / chemistry; Sensitivity and Specificity; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry
TL;DR: The results demonstrate the feasibility of the octylcarboxyamidomethyl modification to improve limits of detection for cysteine-containing peptides with hydrophobic alkyl tags. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, NC State University Libraries
Added: August 6, 2018

2007 journal article

Asymmetric synthesis of C-2-symmetric vicinal diamines via reductive dimerization of N-acylpyridinium and related salts

ORGANIC LETTERS, 10(2), 221–223.

By: P. Bharathi n & D. Comins n

MeSH headings : Catalysis; Diamines / chemical synthesis; Diamines / chemistry; Dimerization; Molecular Structure; Pyridinium Compounds / chemistry; Salts / chemistry; Stereoisomerism
TL;DR: A new route to C2-symmetric diamines via an asymmetric reductive dimerization of 1-acylpyridinium salts and their benzo derivatives is described, practical as the starting heterocycles and chiral auxiliaries are readily available. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2007 journal article

Insecticidal activity and mode of action of novel nicotinoids synthesized by new acylpyridinium salt chemistry and directed lithiation

PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 87(3), 211–219.

By: C. Stumpf n, D. Comins n, T. Sparks, K. Donohue n & R. Roe n

author keywords: nicotinoid; neonicotinoid; nicotine; acetamiprid; insecticidal activity; mode of action; green peach aphid; cotton aphid; western flower thrips; corn earworm; beet armyworm; house fly
TL;DR: It is demonstrated that the new chemistry enhances the insecticidal activity of nicotine with an apparent mode of action as an acetylcholine agonist. (via Semantic Scholar)
UN Sustainable Development Goal Categories
15. Life on Land (Web of Science)
Sources: Web Of Science, NC State University Libraries
Added: August 6, 2018

2007 journal article

One-pot terminal alkene homologation using a tandem olefin cross-metathesis/allylic carbonate reduction sequence

CHEMICAL COMMUNICATIONS, (40), 4170–4171.

By: D. Comins n, J. Dinsmore n & L. Marks n

MeSH headings : Alkenes / chemistry; Carbonates / chemistry; Cross-Linking Reagents / chemistry; Microscopy, Electron, Transmission; Molecular Structure; Oxidation-Reduction; Spectrum Analysis; Titrimetry
TL;DR: A one-carbon homologation of terminal alkenes has been developed utilizing an olefin cross-metathesis followed by a palladium-mediated allylic carbonate reduction. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2007 journal article

Recent advances in the synthesis of nicotine and its derivatives

TETRAHEDRON, 63(34), 8065–8082.

By: F. Wagner n & D. Comins n

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2007 patent

Regioselective halogenation of nicotine and substituted nicotines

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins, F. Fevrier & E. Smith

Source: NC State University Libraries
Added: August 6, 2018

2007 patent

Regiospecific synthesis of nicotine derivatives

Washington, DC: U.S. Patent and Trademark Office.

By: L. King, E. Smith & D. Comins

Source: NC State University Libraries
Added: August 6, 2018

2007 journal article

Synthesis of the benzo-fused indolizidine alkaloid mimics

Beilstein Journal of Organic Chemistry, 3.

By: D. Comins & K. Higuchi

Source: NC State University Libraries
Added: August 6, 2018

2006 journal article

A six-step synthesis of (S)-5-ethenyl-3-(1-methy1-2-pyrrolidinyl)pyridine (SIB-1508Y) from (S)-nicotine

TETRAHEDRON LETTERS, 47(9), 1449–1451.

By: D. Comins n & E. Smith n

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2006 journal article

Expedient five-step synthesis of SIB-1508Y from natural nicotine

JOURNAL OF ORGANIC CHEMISTRY, 71(22), 8673–8675.

By: F. Wagner n & D. Comins n

MeSH headings : Antiparkinson Agents / chemical synthesis; Antiparkinson Agents / chemistry; Molecular Structure; Nicotine / chemistry; Pyridines / chemical synthesis; Pyridines / chemistry; Pyrrolidines / chemical synthesis; Pyrrolidines / chemistry; Stereoisomerism
TL;DR: 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. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2006 journal article

Regioselective 5-, 4-, and 2-substitution of (S)-6-chloronicotine and 4-substitution of (S)-5-chloronicotine

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006(16), 3562–3565.

By: F. Wagner & D. Comins n

author keywords: nicotine; lithiation; iodine dance; regioselectivity
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2006 patent

Regioselective halogenation of nicotine and substituted nicotines

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins, F. Fevrier & E. Smith

Source: NC State University Libraries
Added: August 6, 2018

2006 patent

Regiospecific synthesis of nicotine derivatives

Washington, DC: U.S. Patent and Trademark Office.

By: L. King, E. Smith & D. Comins

Source: NC State University Libraries
Added: August 6, 2018

2006 patent

Short synthesis of pyridine-based pharmaceutical intermediates

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & S. Huang

Source: NC State University Libraries
Added: August 6, 2018

2006 journal article

Six-step synthesis of (S)-brevicolline from (S)-nicotine

ORGANIC LETTERS, 8(16), 3549–3552.

By: F. Wagner & D. Comins n

MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Alkaloids / isolation & purification; Carbolines / chemical synthesis; Carbolines / chemistry; Carbolines / isolation & purification; Carex Plant / chemistry; Indoles / chemistry; Indoles / isolation & purification; Molecular Structure; Nicotine / chemistry; Stereoisomerism
TL;DR: A six-step synthesis of (S)-brevicolline from (S) nicotine, followed by successive Suzuki cross-coupling and Buchwald amination reactions, afforded the enantiopure beta-carboline alkaloid, brevicollines. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2006 patent

Synthesis of nicotine derivatives from nicotine

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & E. Smith

Source: NC State University Libraries
Added: August 6, 2018

2006 journal article

Synthetic studies toward (-)-FR901483 using a conjugate allylation to install the C-1 quaternary carbon

JOURNAL OF ORGANIC CHEMISTRY, 71(25), 9393–9402.

By: D. Gotchev n & D. Comins n

MeSH headings : Carbon / chemistry; Magnetic Resonance Spectroscopy; Mass Spectrometry; Organophosphorus Compounds / chemical synthesis; Organophosphorus Compounds / chemistry; Stereoisomerism
TL;DR: Two approaches to the aza-tricyclo dodecane skeleton of (-)-FR901483 are reported, and 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. (via Semantic Scholar)
Source: Web Of Science
Added: August 6, 2018

2005 journal article

A six-step asymmetric synthesis of (+)-hyperaspine

ORGANIC LETTERS, 7(23), 5227–5228.

By: D. Comins n & J. Sahn n

MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Catalysis; Molecular Structure; Piperidines / chemistry; Quinolizines / chemical synthesis; Quinolizines / chemistry; Stereoisomerism
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2005 journal article

Asymmetric synthesis of 3,3-disubstituted isoindolinones

TETRAHEDRON LETTERS, 46(34), 5639–5642.

By: D. Comins n & A. Hiebel n

author keywords: isoindolinones; asymmetric syuthesis; chiral auxiliary
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2005 journal article

Diels-alder reactions of N-acyl-2-alkyl(aryl)-5-vinyl-2,3-dihydro-4-pyridones

JOURNAL OF ORGANIC CHEMISTRY, 70(13), 5221–5234.

By: D. Comins n, J. Kuethe n, T. Miller n, F. Fevrier n & C. Brooks n

MeSH headings : Alcohols / chemical synthesis; Amino Acids / chemical synthesis; Combinatorial Chemistry Techniques; Cyclization; Ketones / chemical synthesis; Molecular Structure; Pyridones / chemistry; Stereoisomerism
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2005 journal article

Regioselective C-2 and C-6 substitution of (S)-nicotine and nicotine derivatives

ORGANIC LETTERS, 7(24), 5457–5460.

By: F. Fevrier n, E. Smith n & D. Comins n

MeSH headings : Combinatorial Chemistry Techniques; Molecular Structure; Nicotine / analogs & derivatives; Nicotine / chemical synthesis; Nicotine / chemistry; Pyridines / chemistry; Stereoisomerism
TL;DR: 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. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2005 journal article

Regioselective lithium-halogen exchange and palladium-catalyzed cross-coupling reactions of 2,4-dihaloquinolines

TETRAHEDRON LETTERS, 46(39), 6697–6699.

By: D. Comins n, J. Nolan n & I. Bori n

author keywords: lithium-halogen exchange; quinolines; cross-coupling; alpha-amino alkoxide
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

2005 patent

Short synthesis of pyridine-based pharmaceutical intermediates

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & S. Huang

Source: NC State University Libraries
Added: August 6, 2018

2005 journal article

Synthesis of C-4 substituted nicotine derivatives via an N-acylpyridinium salt of (S)-nicotine

ORGANIC LETTERS, 7(22), 5059–5062.

By: D. Comins n, L. King n, E. Smith n & F. Fevrier n

MeSH headings : Molecular Structure; Nicotine / analogs & derivatives; Nicotine / chemical synthesis; Nicotine / chemistry; Pyridinium Compounds / chemistry; Silanes / chemistry; Sulfur / chemistry
TL;DR: A variety of novel nicotine derivatives were prepared from (S)-nicotine via a two-step sequence through addition of a cuprate reagent to an N-acylpyridinium salt of nicotine, followed by aromatization with elemental sulfur. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

2005 journal article

Synthesis of nicotine derivatives via reductive disilylation of (S)-nicotine

ORGANIC LETTERS, 8(2), 179–182.

By: E. Smith n, F. Fevrier n & D. Comins n

MeSH headings : Catalysis; Lithium / chemistry; Molecular Structure; Nicotine / analogs & derivatives; Nicotine / chemical synthesis; Nicotine / chemistry; Oxidation-Reduction; Silanes / chemistry; Stereoisomerism
TL;DR: A variety of novel nicotine derivatives were prepared via reductive disilylation of (S)-nicotine via addition of various carbonyl electrophiles and a catalytic amount of TBAF provided either C-5 substituted nicotines or 1,4-dihydronicotine derivatives. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2005 journal article

Tandem directed lithiations of N-boc-1,2-dihydropyridines toward highly functionalized 2,3-dihydro-4-pyridones

ORGANIC LETTERS, 7(25), 5661–5664.

By: D. Young n & D. Comins n

MeSH headings : Catalysis; Hydrocarbons, Chlorinated / chemical synthesis; Hydrocarbons, Chlorinated / chemistry; Lithium / chemistry; Molecular Structure; Pyridines / chemistry; Pyridones / chemical synthesis; Pyridones / chemistry
TL;DR: 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. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2004 journal article

Addition of indolyl and pyrrolyl grignard reagents to 1-acylpyridinium salts

JOURNAL OF ORGANIC CHEMISTRY, 69(8), 2863–2866.

By: J. Kuethe n & D. Comins n

MeSH headings : Indicators and Reagents; Indoles / chemistry; Molecular Structure; Organometallic Compounds / chemistry; Pyridinium Compounds / chemical synthesis; Pyridinium Compounds / chemistry; Pyrroles / chemistry; Stereoisomerism
TL;DR: 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. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2004 journal article

Asymmetric synthesis of 3-substituted isoindolinones: Application to the total synthesis of (+)-lennoxamine

ORGANIC LETTERS, 7(1), 95–98.

By: D. Comins n, S. Schilling n & Y. Zhang n

MeSH headings : Crystallography, X-Ray; Dioxanes / chemical synthesis; Heterocyclic Compounds / chemical synthesis; Indoles / chemical synthesis; Models, Molecular; Stereoisomerism
TL;DR: An anionic chiral auxiliary mediated asymmetric alkylation of carbamate 2 provides 3-substituted isoindolinones 4 in high ee in the first asymmetric synthesis of (+)-lennoxamine. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2004 journal article

Asymmetric total synthesis of (+)-cannabisativine

JOURNAL OF ORGANIC CHEMISTRY, 69(16), 5219–5231.

By: J. Kuethe n & D. Comins n

MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Cannabinoids / chemical synthesis; Cannabinoids / chemistry; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Organometallic Compounds; Pyridinium Compounds; Stereoisomerism
TL;DR: 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. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2004 journal article

Novel heterocyclic systems. Synthesis of 2,7-dimethyl-10-oxa-1,8-diaza-anthracen-9-one and derivatives

TETRAHEDRON, 60(51), 11751–11758.

By: D. Gotchev n & D. Comins n

author keywords: heterocycle; 10-oxa-1,8-diaza-anthracen-9-one; dehydrative cyclization
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2004 patent

Preparation of a camptothecin derivative by intramolecular cyclisation

Washington, DC: U.S. Patent and Trademark Office.

By: F. Fang, E. Huie, S. Xie & D. Comins

Source: NC State University Libraries
Added: August 6, 2018

2004 patent

Short synthesis of pyridine-based pharmaceutical intermediates

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & S. Huang

Source: NC State University Libraries
Added: August 6, 2018

2003 journal article

Diels-Alder reactions of 5-vinyl-1-acyl-2-aryl-2,3-dihydro-4-pyridones: regio- and stereoselective synthesis of octahydroquinolines

ORGANIC LETTERS, 5(3), 321–323.

By: J. Kuethe n, C. Brooks n & D. Comins n

MeSH headings : Molecular Structure; Pyridones / chemistry; Quinolines / chemical synthesis; Quinolines / chemistry; Stereoisomerism
TL;DR: Readily available 5-vinyldihydropyridones 2 undergo Diels-Alder cyclization with various dienophiles to afford novel octahdroquinolines to afford heterocyclic products containing synthetically useful functionality. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2003 patent

Preparation of a camptothecin derivative by intramolecular cyclisation

Washington, DC: U.S. Patent and Trademark Office.

By: F. Fang, E. Huie, S. Xie & D. Comins

Source: NC State University Libraries
Added: August 6, 2018

2003 journal article

Regioselective sonogashira couplings of 2,4-dibromoquinolines. A correction

JOURNAL OF ORGANIC CHEMISTRY, 68(9), 3736–3738.

By: J. Nolan n & D. Comins n

UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

2003 patent

Short synthesis of pyridine-based pharmaceutical intermediates

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & S. Huang

Source: NC State University Libraries
Added: August 6, 2018

2003 journal article

Tandem Diels-Alder cyclization/aromatization reactions of 5-vinyl-1-acyl-2-aryl-2,3-dihydro-4-pyridones

TETRAHEDRON LETTERS, 44(22), 4179–4182.

By: J. Kuethe n & D. Comins n

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2002 journal article

A novel free-radical ring contraction of a cyclic carbamate

JOURNAL OF ORGANIC CHEMISTRY, 67(6), 1972–1973.

By: A. Williams n, T. Grillo n & D. Comins n

MeSH headings : Aza Compounds / chemical synthesis; Aza Compounds / chemistry; Bridged Bicyclo Compounds / chemical synthesis; Bridged Bicyclo Compounds / chemistry; Carbamates / chemistry; Catalysis; Chromatography; Cyclization; Free Radicals; Magnetic Resonance Spectroscopy; Molecular Structure; Piperidones / chemical synthesis; Piperidones / chemistry; Stereoisomerism
TL;DR: During a study on iodocyclocarbamation reactions of 2-styryl-4-piperidones, a novel ring contraction was observed and a three-electron-three-center mechanism is proposed. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

2002 patent

Preparation of a camptothecin derivative by intramolecular cyclisation

Washington, DC: U.S. Patent and Trademark Office.

By: F. Fang, E. Huie, S. Xie & D. Comins

Source: NC State University Libraries
Added: August 6, 2018

2002 journal article

Synthesis and reactions of enantiopure 1-acyl-2- [triaryl(alkyl)silyl]-2,3-dihydro-4-pyridones

Heterocycles, 58(2002 Nov 22), 505–519.

By: D. Comins, M. Killpack, E. Despagnet & E. Zeller

Source: NC State University Libraries
Added: August 6, 2018

2002 journal article

Synthetic applications of chiral 2,3-dihydro-4-pyridones

Current Opinion in Drug Discovery & Development, 5(6), 870–880.

By: S. Joseph & D. Comins

Source: NC State University Libraries
Added: August 6, 2018

2002 journal article

Total synthesis of the putative structure of the lupin alkaloid plumerinine

ORGANIC LETTERS, 4(9), 1611–1613.

By: D. Comins n, X. Zheng n & R. Goehring n

MeSH headings : Alkaloids / chemical synthesis; Asia; Magnetic Resonance Spectroscopy; Mass Spectrometry; Methylation; Models, Molecular; Oxidation-Reduction; Plants, Medicinal / chemistry; Quinazolines / chemical synthesis; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2001 journal article

A practical six-step synthesis of (S)-camptothecin

ORGANIC LETTERS, 3(26), 4255–4257.

By: D. Comins n & J. Nolan n

MeSH headings : Antineoplastic Agents, Phytogenic / chemical synthesis; Antineoplastic Agents, Phytogenic / chemistry; Camptothecin / chemical synthesis; Camptothecin / chemistry; Heterocyclic Compounds / chemistry
TL;DR: An asymmetric synthesis of (S)-camptothecin has been accomplished in six steps starting from two commercially available heterocycles. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2001 journal article

Asymmetric synthesis of (+)-deoxoprosopinine

Journal of Organic Chemistry, 66(20), 6829–6832.

By: D. Comins n, M. Sandelier n & T. Grillo n

MeSH headings : Alkaloids / chemical synthesis; Analgesics / chemical synthesis; Anesthetics / chemical synthesis; Anti-Bacterial Agents / chemical synthesis; Oxidation-Reduction; Piperidines / chemical synthesis; Plants, Medicinal / chemistry; Stereoisomerism
UN Sustainable Development Goal Categories
Source: NC State University Libraries
Added: August 6, 2018

2001 journal article

Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: A concise asymmetric synthesis of (+)-allopumiliotoxin 267A

ORGANIC LETTERS, 3(3), 469–471.

By: D. Comins n, S. Huang n, C. McArdle n & C. Ingalls n

MeSH headings : Alkaloids / chemical synthesis; Animals; Anura; Indolizines; Piperidines; Pyridones / chemistry; Stereoisomerism
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2001 journal article

Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: asymmetric synthesis of 1-deoxynojirimycin

TETRAHEDRON LETTERS, 42(39), 6839–6841.

By: D. Comins n & A. Fulp n

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2001 journal article

Inter- and intramolecular Horner-Wadsworth-Emmons reactions of 5-(diethoxyphosphoryl)-1-acyl-2-alkyl(aryl)-2,3-dihydro-4-pyridones

TETRAHEDRON LETTERS, 42(25), 4115–4118.

By: D. Comins n & C. Ollinger n

UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

2001 journal article

Model studies toward the total synthesis of the Lycopodium alkaloid spirolucidine

ORGANIC LETTERS, 3(20), 3217–3220.

By: D. Comins n & A. Williams n

MeSH headings : Alkaloids / chemical synthesis; Lycopodiaceae / chemistry; Photochemistry; Pyridones / chemistry; Spiro Compounds / chemical synthesis
TL;DR: A strategy for the synthesis of the spirocyclic core of spirolucidine was explored through a model study and the diene 4a was prepared and photolyzed to give the desired [2 + 2] photoadduct 17 containing the correct relative stereochemistry corresponding to spirollucidine. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2001 journal article

Reduction of N-acyl-2,3-dihydro-4-pyridones to N-acyl-4-piperidones using zinc/acetic acid

JOURNAL OF ORGANIC CHEMISTRY, 66(6), 2181–2182.

By: D. Comins n, C. Brooks n & C. Ingalls n

MeSH headings : Acetic Acid / chemistry; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Oxidation-Reduction; Piperidones / chemistry; Pyridones / chemistry; Zinc / chemistry
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2001 journal article

Synthesis and reactivity of N-acyl-5-(1-hydroxyalkyl)-2,3-dihydro-4-pyridones

ORGANIC LETTERS, 3(5), 769–771.

By: D. Comins n, A. Hiebel n & S. Huang n

MeSH headings : Catalysis; Magnetic Resonance Spectroscopy; Mass Spectrometry; Oxidation-Reduction; Pyridones / chemical synthesis
TL;DR: The Nozaki-Hiyama-Kishi reaction was used to prepare the 5-(1-hydroxyalkyl)-2,3-dihydro-4-pyridones 3 and reduction, oxidation, and substitution reactions of 3 were examined. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2000 journal article

Addition of metallo enolates to chiral 1-acylpyridinium salts: Total synthesis of (+)-cannabisativine

ORGANIC LETTERS, 2(6), 855–857.

By: J. Kuethe n & D. Comins n

MeSH headings : Cannabinoids / chemical synthesis; Cannabinoids / chemistry; Organometallic Compounds; Pyridinium Compounds; Stereoisomerism
TL;DR: A novel route to the first asymmetric synthesis of (+)-cannabisativine is described, accomplished with a high degree of regio- and stereoselectivity in 19 steps and 9% overall yield. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2000 journal article

Asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid

TETRAHEDRON LETTERS, 41(19), 3551–3553.

By: C. Brooks n & D. Comins n

author keywords: asymmetric synthesis; pyridinium salts; dihydropyridones; amino acids
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2000 journal article

Asymmetric synthesis of erythro- and threo-2-(1-hydroxyalkyl)piperidines via iodocyclocarbamation of 1-acyl-2-alkenyl-1,2,3,6-tetrahydropyridines

TETRAHEDRON LETTERS, 41(16), 2839–2842.

By: D. Comins n & A. Williams n

author keywords: asymmetric synthesis; pyridinium salts; dihydropyridones; alkaloids; iodocyclocarbamation
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

2000 patent

Preparation of a camptothecin derivative by intramolecular cyclisation

Washington, DC: U.S. Patent and Trademark Office.

By: F. Fang, E. Huie, S. Xie & D. Comins

Source: NC State University Libraries
Added: August 6, 2018

2000 journal article

Total synthesis of (+)-streptazolin

CHEMICAL COMMUNICATIONS, (7), 569–570.

By: S. Huang n & D. Comins n

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

1999 article

Asymmetric synthesis and synthetic utility of 2,3-dihydro-4-pyridones

JOURNAL OF HETEROCYCLIC CHEMISTRY, Vol. 36, pp. 1491–1500.

By: D. Comins n

Source: Web Of Science
Added: August 6, 2018

1999 journal article

Asymmetric synthesis of dienomycin C

TETRAHEDRON LETTERS, 40(2), 217–218.

By: D. Comins n & G. Green n

UN Sustainable Development Goal Categories
2. Zero Hunger (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

1999 personal communication

Asymmetric synthesis of the Lycopodium alkaloid, N-a-acetyl-N-b-methylphlegmarine

Comins, D. L., Libby, A. H., Al-awar, R. S., & Foti, C. J. (1999, April 2).

By: D. Comins n, A. Libby n, R. Al-awar n & C. Foti n

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

1999 journal article

Diastereoselective addition of prochiral metallo enolates to chiral 1-acylpyridinium salts

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 121(11), 2651–2652.

By: D. Comins*, J. Kuethe, H. Hong*, F. Lakner, T. Concolino & A. Rheingold

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

1999 journal article

Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric synthesis of (-)-slaframine

ORGANIC LETTERS, 1(12), 1941–1943.

By: D. Comins n & A. Fulp n

MeSH headings : Alkaloids / chemical synthesis; Mycotoxins / chemical synthesis; Pyridones / chemical synthesis; Rhizoctonia / chemistry; Stereoisomerism
TL;DR: An asymmetric synthesis of (-)-slaframine and N-acetylslafamine has been accomplished starting from an enantiopure dihydropyridone building block using an efficient phenylselenocyclocarbamation reaction. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

1999 journal article

Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric synthesis of benzomorphans

ORGANIC LETTERS, 1(4), 657–659.

By: D. Comins n, Y. Zhang n & S. Joseph n

MeSH headings : Benzomorphans / chemical synthesis; Benzomorphans / chemistry; Pyridones / chemistry; Stereoisomerism
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

1999 journal article

IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids: Asymmetric synthesis of (+)-luciduline

ORGANIC LETTERS, 1(2), 229–231.

By: D. Comins n, C. Brooks n, R. Al-awar n & R. Goehring n

MeSH headings : Mannich Bases; Plants, Medicinal / chemistry; Quinolines / chemical synthesis; Stereoisomerism
TL;DR: The first chiral auxiliary mediated asymmetric synthesis of the naturally occurring Lycopodium alkaloid (+)-luciduline has been accomplished using an IMDA reaction of a chiral dihydropyridine and a subsequent retro-Mannich ring opening. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

1999 journal article

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

Organic Letters, 1(7), 1031–1033.

By: J. Kuethe n & D. Comins n

MeSH headings : Pyridines / chemical synthesis; Pyridines / chemistry; Pyridones / chemistry; Stereoisomerism
TL;DR: 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. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Source: NC State University Libraries
Added: August 6, 2018

1998 journal article

C-3 acetoxylation of N-acyl-2,3-dihydro-4-pyridones

TETRAHEDRON LETTERS, 39(32), 5693–5696.

By: D. Comins n, D. Stolze n, P. Thakker n & C. McArdle n

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

1998 journal article

Intramolecular photocycloaddition of a tethered bis-2,3-dihydro-4-pyridone: Stereochemistry and reactivity of the cycloadduct

TETRAHEDRON LETTERS, 39(3-4), 187–190.

By: D. Comins n, Y. Lee n & P. Boyle n

UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

1998 journal article

Model studies toward the synthesis of N alpha-acetyl-N beta- methylphlegmarine: Addition of cyclohexylmethyl organometallics to 1-acylpyridinium salts

Heterocycles, 48(7), 1313–1317.

By: D. Comins n, C. Foti n & A. Libby n

Source: NC State University Libraries
Added: August 6, 2018

1998 journal article

Photochemical reactions of chiral 2,3-dihydro-4(1H)-pyridones: asymmetric synthesis of (-)-perhydrohistrionicotoxin

CHEMICAL COMMUNICATIONS, (22), 2509–2510.

By: D. Comins*, Y. Zhang* & X. Zheng

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

1997 article

Asymmetric synthesis and synthetic utility of 2,3-dihydro-4-pyridones

Comins, D. L., Joseph, S. P., Hong, H., Alawar, R. S., Foti, C. J., Zhang, Y. M., … GuerraWeltzien, M. (1997, March). PURE AND APPLIED CHEMISTRY, Vol. 69, pp. 477–481.

By: D. Comins n, S. Joseph n, H. Hong n, R. Alawar n, C. Foti n, Y. Zhang n, X. Chen n, D. LaMunyon n, M. GuerraWeltzien n

Source: Web Of Science
Added: August 6, 2018

1997 journal article

Chiral auxiliary mediated Pictet-Spengler reactions - Asymmetric syntheses of (-)-laudanosine, (+)-glaucine and (-)-xylopinine.

TETRAHEDRON, 53(48), 16327–16340.

By: D. Comins n, P. Thakker n, M. Baevsky n & M. Badawi n

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

1997 journal article

Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric syntheses of indolizidine alkaloids (-)-205A, (-)-207A, and (-)-235B

JOURNAL OF ORGANIC CHEMISTRY, 62(23), 8182–8187.

By: D. Comins n, D. LaMunyon n & X. Chen n

TL;DR: Concise asymmetric syntheses of indolizidine alkaloids (-)-205A, (-)-207A, and (-)-235B were accomplished with a high degree of stereocontrol in eleven steps. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

1997 journal article

Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric synthesis of (-)-septicine and (-)-tylophorine

JOURNAL OF ORGANIC CHEMISTRY, 62(21), 7435–7438.

By: D. Comins n, X. Chen n & L. Morgan n

UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: Web Of Science
Added: August 6, 2018

1996 patent

Method of making asymmetric DE ring intermediates for the synthesis of camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins

Source: NC State University Libraries
Added: August 6, 2018

1996 patent

Method of making asymmetric DE ring intermediates for the synthesis of camptothecin and camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins

Source: NC State University Libraries
Added: August 6, 2018

1995 patent

14-halo-camptothecins

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins

Source: NC State University Libraries
Added: August 6, 2018

1995 patent

Camptothecin intermediates and method of making camptothecin and comptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baevsky

Source: NC State University Libraries
Added: August 6, 2018

1995 patent

Method of making asymmetric de ring intermediates for the synthesis of camptothecin and camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins

Source: NC State University Libraries
Added: August 6, 2018

1995 patent

Method of making intermediates for camptothecin and its analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baevsky

Source: NC State University Libraries
Added: August 6, 2018

1994 patent

Process for making DE ring intermediates for the synthesis of camptothecin and camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baesky

Source: NC State University Libraries
Added: August 6, 2018

1994 patent

Pyridinecarboxaldehyde D-ring intermediates useful for the synthesis of camptothecin and camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baevsky

Source: NC State University Libraries
Added: August 6, 2018

1993 patent

Alkoxymethylpyridine d-ring intermediates useful for the synthesis of camptpthecin and camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baesky

Source: NC State University Libraries
Added: August 6, 2018

1993 patent

Alkylpyridone DE ring intermediates useful for the manufacture of camptothecin and camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baesky

Source: NC State University Libraries
Added: August 6, 2018

1993 patent

Camptothecin intermediate and method of making camptothecin intermediates

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baesky

Source: NC State University Libraries
Added: August 6, 2018

1993 patent

Camptothecin intermediates and method of making same

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baesky

Source: NC State University Libraries
Added: August 6, 2018

1993 patent

Cycloalkyl-based chiral auxiliaries and method making the same

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & J. Salvador

Source: NC State University Libraries
Added: August 6, 2018

1993 patent

D ring intermediates for the synthesis of camptothecin and camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baevsky

Source: NC State University Libraries
Added: August 6, 2018

1993 patent

Method of making intermediates useful for the manufacture of camptothecin and camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baesky

Source: NC State University Libraries
Added: August 6, 2018

1993 patent

Methods and intermediates for the assymmetric synthesis of camptothecin and camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baesky

Source: NC State University Libraries
Added: August 6, 2018

1993 patent

Optically pure D,E ring intermediates useful for the synthesis of camptothecin and camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baesky

Source: NC State University Libraries
Added: August 6, 2018

1992 patent

Intermediates and method of making camptothecin and camptothecin analogs

Washington, DC: U.S. Patent and Trademark Office.

By: D. Comins & M. Baesky

Source: NC State University Libraries
Added: August 6, 2018

1992 journal article

PYRIDINE-DERIVED TRIFLATING REAGENTS - AN IMPROVED PREPARATION OF VINYL TRIFLATES FROM METALLO ENOLATES

TETRAHEDRON LETTERS, 33(42), 6299–6302.

By: D. Comins n & A. Dehghani n

UN Sustainable Development Goal Categories
Source: Web Of Science
Added: August 6, 2018

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