2024 article

Expanded library of novel 2,3-pyrrolidinedione analogues exhibit anti-biofilm activity

Nie, M., Valdes-Pena, M. A., Frohock, B. H., Smits, E., Daiker, J. C., Gilbertie, J. M., … Pierce, J. G. (2024, February 1). BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, Vol. 99.

By: M. Nie n, M. Valdes-Pena n, B. Frohock n, E. Smits n, J. Daiker n, J. Gilbertie n, L. V. Schnabel n, J. Pierce n

author keywords: Natural products; Antibiotics; Antimicrobial resistance; Biofilms; 2 3-pyrrolidinedione
TL;DR: A new library of 2,3-pyrrolidinedione analogues is reported that expands on the previous report on the antimicrobial studies of this heterocyclic scaffold and displayed antibiofilm properties and represent intriguing scaffolds for further optimization and development. (via Semantic Scholar)
Sources: ORCID, Web Of Science
Added: January 7, 2024

2024 article

Total Synthesis and Microbiological Evaluation of Leopolic Acid A and Analogues

Breunig, J. L., Valdes-Pena, M. A., Ratchford, A. W., & Pierce, J. G. (2024, January 12). ACS BIO & MED CHEM AU, Vol. 1.

By: J. Breunig n, M. Valdes-Pena n, A. Ratchford n & J. Pierce n

author keywords: antibiotics; antibiofilm; naturalproducts; multicomponent reactions; heterocycles
Sources: ORCID, Web Of Science
Added: January 13, 2024

2023 journal article

3-Component Approach to 1,5-Dihydro-2<i>H</i>-pyrrol-2-one Heterocycles

ORGANIC SYNTHESES, 100, 418-+.

By: N. Massaro* & J. Pierce

Sources: Web Of Science, ORCID
Added: March 4, 2024

2023 journal article

Photoredox Catalyzed C(sp<SUP>3</SUP>)-C(sp<SUP>3</SUP>) Coupling of α-Bromoesters and Triethylamine

JOURNAL OF ORGANIC CHEMISTRY, 89(1), 810–814.

By: A. Guerra n & J. Pierce n

Sources: ORCID, Web Of Science
Added: December 22, 2023

2023 article

Using Stem Mini-Organs to Find New Cures

Piedrahita, J., & Pierce, J. (2023, August 4).

By: J. Piedrahita n & J. Pierce n

Source: ORCID
Added: August 11, 2023

2022 article

Chemistry Drives Solutions to Our Planet’s Largest Problems: COVID-19 and Beyond

Pierce, J. (2022, June 22).

By: J. Pierce n

Source: ORCID
Added: August 17, 2022

2022 journal article

Restoring Carboxylates on Highly Modified Alginates Improves Gelation, Tissue Retention and Systemic Capture

ACTA BIOMATERIALIA, 138, 208–217.

By: C. Moody n, A. Brown n, N. Massaro n, A. Patel n, P. Agarwalla n, A. Simpson n, A. Brown n, H. Zheng n, J. Pierce n, Y. Brudno n

author keywords: Alginate; Click chemistry; Bioconjugation; Ionic cross-linking; Drug capture
UN Sustainable Development Goal Categories
Sources: ORCID, Web Of Science
Added: October 31, 2021

2022 article

Synthesis provides insight into a traditional medicine

Onuska, N. P. R., & Pierce, J. G. (2022, June 30). NATURE, Vol. 606, pp. 869–870.

By: N. Onuska n & J. Pierce n

author keywords: Chemical biology; Organic chemistry; Chemistry; Synthesis
MeSH headings : Chemistry Techniques, Synthetic; Medicine, Traditional; Molecular Targeted Therapy / trends
Sources: Web Of Science, ORCID
Added: July 11, 2022

2022 journal article

Tissue-reactive drugs enable materials-free local depots

JOURNAL OF CONTROLLED RELEASE, 343, 142–151.

By: S. Pandit n, S. Palvai n, N. Massaro n, J. Pierce n & Y. Brudno n

author keywords: Sustained release; Materials-free delivery; Paclitaxel; Pancreatic cancer; Extracellular matrix; N-hydroxysuccinimide ester
MeSH headings : Animals; Cell Line, Tumor; Drug Delivery Systems; Drug Liberation; Hydrogels; Mice; Paclitaxel; Pancreatic Neoplasms / drug therapy
TL;DR: It is demonstrated that locally injected TRAPs create dispersed, stable intratumoral depots deep within mouse and human pancreatic tumor tissues, and had better solubility than free paclitaxel and enabled sustained in vitro and in vivo drug release. (via Semantic Scholar)
UN Sustainable Development Goal Categories
3. Good Health and Well-being (Web of Science; OpenAlex)
Sources: Web Of Science, ORCID
Added: May 2, 2022

2022 article

Total Synthesis of Bipolamine I

Pierce, J. G., & Qiu, X. (2022, July 5). JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Vol. 7.

By: J. Pierce n & X. Qiu n

MeSH headings : Alkaloids; Biological Products; Polymers; Pyrroles; Stereoisomerism
TL;DR: A stereoselective 15-step synthesis of bipolamine I, a distinct member of the broader family, and through this work develop an intermediate that will serve to access other polypyrrole natural products and key analogues going forward. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: ORCID, Web Of Science
Added: July 6, 2022

2021 journal article

Design, synthesis, and evaluation of substrate - analogue inhibitors of Trypanosoma cruzi ribose 5-phosphate isomerase type B

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 32.

By: S. Natalia Gonzalez*, J. Mills n, D. Maugeri*, C. Olaya n, B. Laguera*, J. Enders n, J. Sherman, A. Rodriguez ...

author keywords: Neglected tropical diseases; Chagas' disease; Trypanosoma cruzi; Amastigote; Trypomastigote; Isomerase; Substrate-analogue inhibitors; Competitive inhibition; Trypsin digestion LC-MS/MS
MeSH headings : 3T3 Cells; Aldose-Ketose Isomerases / antagonists & inhibitors; Aldose-Ketose Isomerases / metabolism; Animals; Binding Sites; Catalytic Domain; Drug Design; Enzyme Inhibitors / chemistry; Enzyme Inhibitors / metabolism; Enzyme Inhibitors / pharmacology; Kinetics; Mice; Molecular Dynamics Simulation; Protozoan Proteins / antagonists & inhibitors; Protozoan Proteins / metabolism; Substrate Specificity; Trypanocidal Agents / chemical synthesis; Trypanocidal Agents / metabolism; Trypanocidal Agents / pharmacology; Trypanosoma cruzi / drug effects; Trypanosoma cruzi / enzymology
TL;DR: The study of Compound B served as a proof-of-concept so that next generation inhibitors can potentially be developed with a focus on using a prodrug group in replacement of the iodoacetamide moiety, thus representing an attractive starting point for the future treatment of Chagas' disease. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: ORCID, Web Of Science
Added: December 15, 2020

2021 review

Leveraging Marine Natural Products as a Platform to Tackle Bacterial Resistance and Persistence

[Review of ]. ACCOUNTS OF CHEMICAL RESEARCH, 54(8), 1866–1877.

By: M. Valdes-Pena n, N. Massaro n, Y. Lin n & J. Pierce n

MeSH headings : Alkaloids / chemical synthesis; Alkaloids / pharmacology; Anti-Bacterial Agents / chemical synthesis; Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / pharmacology; Biofilms / drug effects; Biological Products / chemical synthesis; Biological Products / chemistry; Biological Products / pharmacology; Drug Resistance, Multiple, Bacterial / drug effects; Guanidine / analogs & derivatives; Guanidine / chemical synthesis; Guanidine / pharmacology; Guanidines / chemical synthesis; Guanidines / pharmacology; Microbial Sensitivity Tests; Oxazolidinones / chemical synthesis; Oxazolidinones / pharmacology; Staphylococcus aureus / drug effects; Staphylococcus aureus / physiology; Stereoisomerism; Structure-Activity Relationship
TL;DR: These studies provide several distinct platforms for the development of novel therapeutics that can add to the arsenal of scaffolds for preclinical development and can provide insight into the biochemical processes and pathways that can be targeted by small molecules in the fight against antimicrobial-resistant and -tolerant infections. (via Semantic Scholar)
UN Sustainable Development Goal Categories
14. Life Below Water (OpenAlex)
Sources: ORCID, Web Of Science
Added: March 19, 2021

2021 journal article

Rapid synthesis of the core scaffold of crinane and haemanthamine through a multi-component approach

TETRAHEDRON LETTERS, 75.

By: N. Massaro n & J. Pierce n

author keywords: Amaryllidaceae alkaloids; Heterocycles; Multicomponent; Natural products; Total synthesis
TL;DR: A key highlight of the approach is the modularity of the core synthesis, overcoming existing challenges for these scaffolds and providing a path to explore site-selective oxidation to expand the scope of molecules accessible from common intermediates. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: ORCID, Web Of Science
Added: May 25, 2021

2021 journal article

Stereoselective Synthesis of the Spirocyclic gamma-Lactam Core of the Ansalactams

ORGANIC LETTERS, 23(24), 9559–9562.

By: Z. Liang n, Y. Lin n & J. Pierce n

MeSH headings : Spiro Compounds
TL;DR: The development of a stereoselective formal [3+2] cycloaddition reaction for the construction of this key spiro-γ-lactam motif for the first time is reported, thereby enabling access to the northern domain of ansalactam A. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: ORCID, Web Of Science
Added: December 1, 2021

2020 chapter

1,4-Oxazines and their Benzo Derivatives

In Comprehensive Heterocyclic Chemistry IV.

By: Y. Lin, C. Martinez-Brokaw & J. Pierce

Sources: Crossref, ORCID
Added: December 24, 2020

2020 journal article

Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D: Development of a Stereodivergent Strategy

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 142(21), 9850–9857.

By: Y. Lin n, A. Ribaucourt n, Y. Moazami n & J. Pierce n

MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Alkaloids / pharmacology; Anti-Bacterial Agents / chemical synthesis; Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / pharmacology; Microbial Sensitivity Tests; Molecular Conformation; Pyrimidines / chemical synthesis; Pyrimidines / chemistry; Pyrimidines / pharmacology; Staphylococcus aureus / drug effects; Stereoisomerism
TL;DR: The stereocontrolled synthesis allowed for the investigation of the antimicrobial activity of batzelladine D, demonstrating promising activity that is more potent for non-natural stereoisomers. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: June 22, 2020

2020 journal article

Front Cover: 5‐Benzylidene‐4‐Oxazolidinones Are Synergistic with Antibiotics for the Treatment of Staphylococcus aureus Biofilms (ChemBioChem 7/2020)

ChemBioChem.

By: B. Frohock n, J. Gilbertie n, J. Daiker n, L. Schnabel n & J. Pierce n

Source: ORCID
Added: December 15, 2020

2020 journal article

Genetic Determinants of Salmonella Resistance to the Biofilm-Inhibitory Effects of a Synthetic 4-Oxazolidinone Analog

Applied and Environmental Microbiology, 86(20).

By: K. Griewisch n, J. Pierce n & J. Elfenbein n

Ed(s): M. Kivisaar

author keywords: Salmonella; antimicrobial resistance; biofilm; genetics
MeSH headings : Anti-Bacterial Agents / pharmacology; Biofilms / drug effects; Drug Resistance, Bacterial / genetics; Oxazolidinones / pharmacology; Salmonella typhimurium / drug effects; Salmonella typhimurium / genetics
TL;DR: The results of this study suggest that JJM-ox-3-70 inhibits biofilm formation by indirect inhibition of extracellular matrix production that may be linked to disruption of flagellar motility. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: ORCID, Crossref, Web Of Science
Added: November 16, 2020

2020 journal article

In Vitro Evaluation of a Novel Synthetic Bilirubin Analog as an Antioxidant and Cytoprotective Agent for Pancreatic Islet Transplantation

Cell Transplantation, 29, 096368972090641.

By: E. Luckring n, P. Parker n, H. Hani*, M. Grace n, M. Lila n, J. Pierce n, C. Adin*

Contributors: E. Luckring n, P. Parker n, H. Hani*, M. Grace n, M. Lila n, J. Pierce n, C. Adin*

MeSH headings : Animals; Antioxidants / chemical synthesis; Antioxidants / chemistry; Bilirubin / analogs & derivatives; Bilirubin / chemical synthesis; Bilirubin / chemistry; Cell Survival / physiology; Fluorescence Recovery After Photobleaching; Islets of Langerhans Transplantation / methods; Molecular Structure; Swine
TL;DR: Two bilirubin analogs are synthesized that can be produced without the use of animal-derived products and have promising antioxidant and cytoprotective effects, limiting islet cell death in a model of islet transplantation hypoxic stress. (via Semantic Scholar)
Source: ORCID
Added: July 9, 2020

2020 journal article

Stereocontrolled Synthesis of (±)-Melokhanine E via an Intramolecular Formal [3 + 2] Cycloaddition

Organic Letters, 22(2), 714–717.

By: A. Cholewczynski n, P. Williams n & J. Pierce n

MeSH headings : Cycloaddition Reaction; Cyclopropanes / chemistry; Imines / chemistry; Molecular Structure; Secologanin Tryptamine Alkaloids / chemical synthesis; Secologanin Tryptamine Alkaloids / chemistry; Stereoisomerism
TL;DR: The reported efforts serve as a synthetic platform to prepare an array of alkaloids bearing this core structural motif to enable stereoselective construction of the core scaffold through a formal [3 + 2] cycloaddition. (via Semantic Scholar)
Source: ORCID
Added: December 15, 2020

2020 journal article

Stereoselective, Multicomponent Approach to Quaternary Substituted Hydroindole Scaffolds

ORGANIC LETTERS, 22(13), 5079–5084.

By: N. Massaro n & J. Pierce n

MeSH headings : Amaryllidaceae Alkaloids / chemistry; Indoles / chemical synthesis; Indoles / chemistry; Stereoisomerism
TL;DR: A highly convergent, diastereoselective, multicomponent approach to access the hydroindole cores present within crinine, haemanthamine, pretazettine, and various other bioactive alkaloids. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 3, 2020

2019 article

5-Benzylidene-4-Oxazolidinones Are Synergistic with Antibiotics for the Treatment of Staphylococcus aureus Biofilms

CHEMBIOCHEM, Vol. 12.

By: B. Frohock n, J. Gilbertie n, J. Daiker n, L. Schnabel n & J. Pierce n

MeSH headings : Acinetobacter baumannii / drug effects; Anti-Bacterial Agents / pharmacology; Benzylidene Compounds / pharmacology; Biofilms / drug effects; Drug Synergism; Methicillin-Resistant Staphylococcus aureus / drug effects; Microbial Sensitivity Tests; Oxazolidinones / pharmacology; Staphylococcus aureus / physiology; Structure-Activity Relationship
TL;DR: An expanded set of 5‐benzylidene‐4‐oxazolidinones is reported that is able to inhibit the formation of Staphylococcus aureus biofilms, disperse preformed biofilm, and are able to significantly reduce the bacterial load in a robust collagen‐matrix model of biofilm infection. (via Semantic Scholar)
UN Sustainable Development Goal Categories
3. Good Health and Well-being (Web of Science; OpenAlex)
Sources: ORCID, Web Of Science
Added: January 13, 2020

2019 journal article

5-Benzylidene-4-Oxazolidinones are Synergistic with Antibiotics for the Treatment of Staphylococcus Aureus Biofilms

[Preprint]. 9.

By: B. Frohock n, J. Gilbertie n, J. Daiker n, L. Schnabel n & J. Pierce n

UN Sustainable Development Goal Categories
3. Good Health and Well-being (OpenAlex)
Sources: Crossref, ORCID
Added: December 22, 2020

2019 journal article

Accidental intoxications in toddlers: lack of cross-reactivity of vilazodone and its urinary metabolite M17 with drug of abuse screening immunoassays

BMC CLINICAL PATHOLOGY, 19.

By: C. Martinez-Brokaw n, J. Radke*, J. Pierce n, A. Ehlers*, S. Ekins*, K. Wood*, J. Maakestad*, J. Rymer*, K. Tamama*, M. Krasowski*

author keywords: Amphetamines; False positive reactions; Immunoassay; Similarity; Toxicology
TL;DR: While the vilazodone metabolite M17 has weak 2D structural similarity to amphetamines and tricyclic antidepressants, the current study did not demonstrate any experimental cross-reactivity with two different urine Amphetamines immunoassays and a serum tricycleclic antidepressant immunoASSay. (via Semantic Scholar)
UN Sustainable Development Goal Categories
3. Good Health and Well-being (Web of Science; OpenAlex)
Sources: Web Of Science, ORCID
Added: March 4, 2019

2019 article

Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D

Pierce, J., & Lin, Y.-C. (2019, October 3). (Vol. 10). Vol. 10.

By: J. Pierce n & Y. Lin n

Source: ORCID
Added: October 22, 2021

2019 article

Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D

Lin, Y.-C., Ribaucourt, A., Moazami, Y., & Pierce, J. (2019, October 4).

By: Y. Lin, A. Ribaucourt, Y. Moazami & J. Pierce n

TL;DR: The stereo-controlled synthesis allowed for the investigation of the antimicrobial activity of batzelladine D, demonstrating promising activity that is more potent for non-natural stereoisomers. (via Semantic Scholar)
Source: ORCID
Added: October 22, 2021

2019 journal article

Expanded Structure-Activity Studies of Lipoxazolidinone Antibiotics

ACS MEDICINAL CHEMISTRY LETTERS, 10(3), 374-+.

By: K. Robinson n, J. Mills n & J. Pierce n

author keywords: Oxazolidinones; antibiotics; MRSA; heterocycles
TL;DR: This work expanded previous synthetic efforts by preparing selected aryl derivatives of the lipoxazolidinones and further evaluating the potential to expand the activity of this class of molecules to Gram-negative pathogens, and utilized a TolC knockout strain of E. coli to demonstrate that these compounds are subject to efflux in Gram- negative pathogens. (via Semantic Scholar)
UN Sustainable Development Goal Categories
14. Life Below Water (OpenAlex)
Sources: Web Of Science, ORCID
Added: April 2, 2019

2019 journal article

Stereocontrolled Synthesis of Melokhanine E via an Intramolecular Formal [3+2] Cycloaddition

[Preprint]. 10.

By: J. Pierce n, A. Cholewczynski & P. Williams

Sources: Crossref, ORCID
Added: December 22, 2020

2018 journal article

3-Hydroxy-1,5-dihydro-2H-pyrrol-2-ones as novel antibacterial scaffolds against methicillin-resistant Staphylococcus aureus

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 28(16), 2732–2735.

By: A. Cusumano n & J. Pierce n

author keywords: Natural products; Antibiotics; Heterocycles; Cyclization; Medicinal chemistry
MeSH headings : Anti-Bacterial Agents / chemical synthesis; Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / pharmacology; Dose-Response Relationship, Drug; Methicillin Resistance / drug effects; Methicillin-Resistant Staphylococcus aureus / drug effects; Microbial Sensitivity Tests; Molecular Structure; Pyrroles / chemical synthesis; Pyrroles / chemistry; Pyrroles / pharmacology; Staphylococcus epidermidis / drug effects; Structure-Activity Relationship
TL;DR: These molecules, previously underexplored as antibacterial agents, serve as a new scaffold for antimicrobial development. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: October 19, 2018

2018 journal article

Coupling of thioamides with 4-bromocrotonate esters and subsequent conjugate addition for the rapid one-pot synthesis of functionalized thiazolines

Tetrahedron Letters, 59(3), 277–279.

By: P. Parker n, Y. Ge n & J. Pierce n

author keywords: Heterocycle; Natural products; Medicinal chemistry; Alkylation; Thiazoline
TL;DR: An efficient one-pot synthesis of functionalized thiazolines via the coupling of thioamides with 4-bromocrotonate esters with the presence of the exocyclic ester functionality provides a convenient handle for the synthesis of more complex thiazoline-containing natural products and biologically-relevant compounds. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Crossref, ORCID
Added: February 24, 2020

2018 journal article

Mast cell degranulation and calcium influx are inhibited by an Echinacea purpurea extract and the alkylamide dodeca-2E,4E-dienoic acid isobutylamide

Journal of Ethnopharmacology, 212, 166–174.

By: T. Gulledge n, N. Collette n, E. Mackey*, S. Johnstone n, Y. Moazami n, D. Todd*, A. Moeser*, J. Pierce n, N. Cech*, S. Laster n

author keywords: Alkylamide; Echinacea purpurea; Allergies; Inflammation; Mast cell
MeSH headings : Amides / chemistry; Amides / pharmacology; Animals; Calcium / metabolism; Cell Line; Dinoprostone / genetics; Dinoprostone / metabolism; Echinacea / chemistry; Female; Gene Expression Regulation / drug effects; Humans; Male; Mast Cells / drug effects; Mice; Plant Extracts / chemistry; Plant Extracts / pharmacology; Rats; Tumor Necrosis Factor-alpha / genetics; Tumor Necrosis Factor-alpha / metabolism
TL;DR: It is suggested that Echinacea extracts and alkylamides may be useful for treating allergic and inflammatory responses mediated by mast cells and the inhibitory effects of alkyamides on calcium uptake would be predicted to dampen a variety of pathological responses. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: February 21, 2020

2018 journal article

Synthesis and Biological Evaluation of the Antimicrobial Natural Product Lipoxazolidinone A

Angewandte Chemie, 130(28), 8818–8822.

By: J. Mills n, K. Robinson n, T. Zehnder n & J. Pierce n

UN Sustainable Development Goal Categories
14. Life Below Water (OpenAlex)
Source: ORCID
Added: December 15, 2020

2018 article

Synthesis and Biological Evaluation of the Antimicrobial Natural Product Lipoxazolidinone A

Mills, J. J., Robinson, K. R., Zehnder, T. E., & Pierce, J. G. (2018, April 9).

By: J. Mills, K. Robinson, T. Zehnder & J. Pierce n

UN Sustainable Development Goal Categories
14. Life Below Water (OpenAlex)
Source: ORCID
Added: October 21, 2021

2018 journal article

Synthesis and Biological Evaluation of the Antimicrobial Natural Product Lipoxazolidinone A

Angewandte Chemie International Edition, 57(28), 8682–8686.

By: J. Mills n, K. Robinson n, T. Zehnder n & J. Pierce n

author keywords: antibiotics; cyclization; heterocycles; medicinal chemistry; natural products
MeSH headings : Anti-Bacterial Agents / chemical synthesis; Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / pharmacology; Biological Products / chemical synthesis; Biological Products / chemistry; Biological Products / pharmacology; Methicillin-Resistant Staphylococcus aureus / drug effects; Microbial Sensitivity Tests; Molecular Structure; Oxazolidinones / chemical synthesis; Oxazolidinones / chemistry; Oxazolidinones / pharmacology; Structure-Activity Relationship
TL;DR: The first synthesis of lipoxazolidinone A is reported, with 15 structural analogues to explore its active pharmacophore, and initial resistance and mechanism of action studies suggest that 4-oxzolidinones are valuable scaffolds for antimicrobial development and reveal simplified lead compounds for further optimization. (via Semantic Scholar)
UN Sustainable Development Goal Categories
14. Life Below Water (OpenAlex)
Sources: Web Of Science, ORCID, Crossref
Added: August 6, 2018

2018 journal article

Synthesis of Quaternary-Substituted Thiazolines via Halocyclization of S-Allyl Thioimidate Salts

The Journal of Organic Chemistry, 83(1), 12–22.

By: P. Parker n, B. Lemercier n & J. Pierce n

TL;DR: An efficient synthesis of S-allyl thioimidate hydrobromide salts via coupling of thioamides with allyl bromide derivatives is described, providing a variety of substituted alkyl- and arylthiazolines. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Crossref, ORCID
Added: December 11, 2020

2017 journal article

5-Benzylidene-4-oxazolidinones potently inhibit biofilm formation in Methicillin-resistant Staphylococcus aureus

Chemical Communications, 53(53), 7353–7356.

By: G. Edwards n, N. Shymanska n & J. Pierce n

MeSH headings : Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / pharmacology; Benzylidene Compounds / chemistry; Benzylidene Compounds / pharmacology; Biofilms / drug effects; Dose-Response Relationship, Drug; Methicillin-Resistant Staphylococcus aureus / drug effects; Microbial Sensitivity Tests; Molecular Structure; Oxazolidinones / chemistry; Oxazolidinones / pharmacology; Structure-Activity Relationship
TL;DR: Together, these results suggest that 4-oxazolidinones represent new chemotypes to enable the study of bacterial biofilms with small molecule chemical probes. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: February 24, 2020

2017 journal article

Direct Access to Highly Functionalized Heterocycles through the Condensation of Cyclic Imines and alpha-Oxoesters

JOURNAL OF ORGANIC CHEMISTRY, 82(24), 13714–13721.

By: A. Cusumano n, M. Boudreau n & J. Pierce n

MeSH headings : Cyclization; Heterocyclic Compounds / chemistry; Imines / chemistry; Molecular Structure
TL;DR: A facile, gram-scale preparation from a condensation cyclization of α-oxoesters with five- and six-membered cyclic imines enables a concise, three-step synthesis of the natural products phenopyrrozin and p-hydroxyphenopyr rozin. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2017 journal article

How Cancer Cells Become Resistant to Cationic Lytic Peptides: It’s the Sugar!

Cell Chemical Biology, 24(2), 121–122.

By: J. Pierce n

MeSH headings : Cell Line, Tumor; Cell Membrane; Peptides; Polysaccharides; Sugars
TL;DR: This study provides the first insight into potential resistance mechanisms toward cationic lytic peptides and highlights the important, yet previously unappreciated, role cell-surface glycans can play in cellular resistance mechanisms. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: December 11, 2020

2017 journal article

Stereoselective Synthesis of Quaternary Pyrrolidine-2,3-diones and beta-Amino Acids

ORGANIC LETTERS, 19(11), 2961–2964.

By: N. Shymanska n & J. Pierce n

MeSH headings : Amino Acids; Cyclization; Molecular Structure; Pyrrolidines / chemistry; Stereoisomerism
TL;DR: A facile, diastereoselective synthesis of highly substituted pyrrolidine-2,3-diones is reported, along with the one-step conversion of these heterocycles to novel β-amino acids and further functionalized derivatives. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2017 journal article

Structure, synthesis and biological properties of the pentacyclic guanidinium alkaloids

Bioorganic & Medicinal Chemistry, 25(11), 2817–2824.

By: Y. Shi n, Y. Moazami n & J. Pierce n

author keywords: Guanidinium alkaloids; Marine natural products; Chemical probe; Structure-activity relationship; Mechanism of action
MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Alkaloids / pharmacology; Animals; Anti-Bacterial Agents / chemical synthesis; Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / pharmacology; Antifungal Agents / chemical synthesis; Antifungal Agents / chemistry; Antifungal Agents / pharmacology; Antineoplastic Agents / chemical synthesis; Antineoplastic Agents / chemistry; Antineoplastic Agents / pharmacology; Antiprotozoal Agents / chemical synthesis; Antiprotozoal Agents / chemistry; Antiprotozoal Agents / pharmacology; Antiviral Agents / chemical synthesis; Antiviral Agents / chemistry; Antiviral Agents / pharmacology; Guanidine / chemical synthesis; Guanidine / chemistry; Guanidine / pharmacology; Humans; Molecular Structure; Structure-Activity Relationship
TL;DR: The structure, synthesis, toxicity and mechanisms of action of PGAs are summarized and their potential as chemical probes and/or therapeutic leads are highlighted. (via Semantic Scholar)
UN Sustainable Development Goal Categories
14. Life Below Water (OpenAlex)
Sources: Crossref, ORCID
Added: February 24, 2020

2016 journal article

Examining ubiquitinated peptide enrichment efficiency through an epitope labeled protein

ANALYTICAL BIOCHEMISTRY, 512, 114–119.

By: J. Parker n, Y. Oh n, Y. Moazami n, J. Pierce n, P. Loziuk n, R. Dean n, D. Muddiman n

author keywords: Ubiquitination; Gly-Gly enrichment; Enrichment efficiency
MeSH headings : Antibodies, Monoclonal, Murine-Derived / chemistry; Epitopes / chemistry; Muramidase / chemistry; Ubiquitinated Proteins / chemistry; Ubiquitination
TL;DR: It is shown that when conjugated to a lysine containing protein, such as lysozyme, it can be applied as a standard protein to examine ubiquitinated peptide enrichment within a complex background. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2016 journal article

Stereocontrolled Synthesis of (+)-Plagiogyrin A

Organic Letters, 18(20), 5308–5311.

By: Y. Shi n & J. Pierce n

TL;DR: The skeleton of Plagiogyrin A is synthesized by employing a stereocontrolled aldol reaction followed by the installation of the α-ketoaldehyde moiety derived from the mild oxidation of an α-diazoketone. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: February 24, 2020

2016 journal article

Synthesis of 1,2,4-Oxadiazoles via DDQ-Mediated Oxidative Cyclization of Amidoximes

Synthesis, 48(12), 1902–1909.

By: J. Pierce n & P. Parker n

author keywords: oxidation; cyclization; heterocycles; radicals; medicinal chemistry
UN Sustainable Development Goal Categories
Sources: Crossref, ORCID, NC State University Libraries
Added: August 6, 2018

2016 journal article

Thiohydroximic acids: Versatile reagents for organic synthesis

Synlett, 27(2), 181–189.

By: B. Lemercier & J. Pierce

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

2015 journal article

Marine natural products synthesis as a driving force for chemical and biological discovery

Planta Medica, 81(11).

By: J. Pierce n, N. Shymanska n & G. Edwards n

UN Sustainable Development Goal Categories
14. Life Below Water (OpenAlex)
Sources: Crossref, ORCID
Added: February 24, 2020

2015 journal article

Rapid synthesis and antimicrobial activity of novel 4-oxazolidinone heterocycles

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 25(21), 4887–4889.

By: N. Shymanska n, I. An n, S. Guevara-Zuluaga n & J. Pierce n

author keywords: Antibiotic; Heterocycle; Oxazolidinone; Natural products
MeSH headings : Acinetobacter baumannii / drug effects; Anti-Bacterial Agents / chemical synthesis; Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / pharmacology; Dose-Response Relationship, Drug; Microbial Sensitivity Tests; Molecular Structure; Oxazolidinones / chemical synthesis; Oxazolidinones / chemistry; Oxazolidinones / pharmacology; Staphylococcus aureus / drug effects; Structure-Activity Relationship
TL;DR: These studies revealed the importance of an electron deficient aromatic ring for antimicrobial activity and serve as the basis for future SAR studies around the 4-oxazolidinone core. (via Semantic Scholar)
UN Sustainable Development Goal Categories
14. Life Below Water (OpenAlex)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2015 journal article

Synthesis and biological evaluation of a series of fatty acid amides from Echinacea

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 25(16), 3091–3094.

By: Y. Moazami n, T. Gulledge n, S. Laster n & J. Pierce n

author keywords: Echinacea; Alkylamide; TNF-alpha; Anti-inflammatory; Cytokine
MeSH headings : Amides / chemical synthesis; Amides / chemistry; Amides / pharmacology; Animals; Cell Line; Echinacea / chemistry; Echinacea / metabolism; Fatty Acids / chemistry; Lipopolysaccharides / toxicity; Macrophages / cytology; Macrophages / drug effects; Macrophages / metabolism; Mice; Plant Extracts / chemistry; Tumor Necrosis Factor-alpha / metabolism
TL;DR: The SAR of simple alkylamides found in Echinacea extracts with respect to their ability to decrease the production of the pro-inflammatory mediator TNF-α is explored. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2015 journal article

Synthesis of 1,4,2-Oxathiazoles via Oxidative Cyclization of Thiohydroximic Acids

ORGANIC LETTERS, 17(18), 4542–4545.

By: B. Lemercier n & J. Pierce n

MeSH headings : Antineoplastic Agents / chemical synthesis; Antineoplastic Agents / chemistry; Catalysis; Copper / chemistry; Cyclization; Molecular Structure; Oxidation-Reduction; Oximes / chemistry; Thiazoles / chemical synthesis; Thiazoles / chemistry
TL;DR: This reaction represents the only method currently available to prepare a diverse set of oxathiazoles and expands the chemistry of C-H oxidation via appended N-OH functional groups. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2015 journal article

Synthesis of 2,3-Dihydro-1,3-oxazin-4-ones via a Mild Formal [4+2] Cycloaddition of Acylketenes with Aldimines

Synthesis, 47(21), 3363–3370.

By: J. Pierce n & Y. Moazami n

author keywords: cycloaddition; heterocycles; imines; transition metals; acylation
Sources: Crossref, ORCID, NC State University Libraries
Added: August 6, 2018

2015 journal article

Synthesis of the 5,6-Dihydroxymorpholin-3-one Fragment of Monanchocidin A

ORGANIC LETTERS, 17(4), 968–971.

By: Y. Shi n & J. Pierce n

MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Guanidine / analogs & derivatives; Guanidine / chemical synthesis; Guanidine / chemistry; Molecular Structure; Morpholines / chemical synthesis; Morpholines / chemistry; Stereoisomerism
TL;DR: A rapid synthesis of this heterocyclic scaffold is reported and its structure is confirmed to be that of a recently isolated pentacyclic guanidinium alkaloid that contains an unusual highly oxidized morpholinone fragment. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2015 journal article

Thiohydroximic Acids: Versatile Reagents for Organic Synthesis

Synlett, 27(02), 181–189.

By: J. Pierce n & B. Lemercier n

author keywords: heterocycles; sulfur; nitrogen; radicals; medicinal chemistry
UN Sustainable Development Goal Categories
Source: Crossref
Added: February 24, 2020

2014 journal article

A Rapid Synthesis of 4-Oxazolidinones: Total Synthesis of Synoxazolidinones A and B**

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 53(21), 5401–5404.

By: N. Shymanska n, I. An n & J. Pierce n

author keywords: antimicrobial agents; heterocycles; natural products; stereoselectivity; total synthesis
MeSH headings : Acinetobacter baumannii / drug effects; Acylation; Anti-Bacterial Agents / chemical synthesis; Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / pharmacology; Cyclization; Guanidine / analogs & derivatives; Guanidine / chemical synthesis; Guanidine / chemistry; Guanidine / pharmacology; Imines / chemistry; Oxazolidinones / chemical synthesis; Oxazolidinones / chemistry; Oxazolidinones / pharmacology; Staphylococcus aureus / drug effects; Stereoisomerism
TL;DR: These studies confirmed the importance of the chlorine substituent for antimicrobial activity and revealed simplified dichloro derivatives that are equally potent against several bacterial strains. (via Semantic Scholar)
UN Sustainable Development Goal Categories
14. Life Below Water (OpenAlex)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2014 journal article

Synthesis of Thiazolines by Copper Catalyzed Aminobromination of Thiohydroximic Acids

ORGANIC LETTERS, 16(7), 2074–2076.

By: B. Lemercier n & J. Pierce n

MeSH headings : Alkenes / chemical synthesis; Amines / chemical synthesis; Catalysis; Combinatorial Chemistry Techniques; Copper / chemistry; Hydrocarbons, Brominated / chemical synthesis; Hydrocarbons, Brominated / chemistry; Molecular Structure; Oximes / chemistry; Stereoisomerism; Thiazolidines / chemical synthesis; Thiazolidines / chemistry
TL;DR: A copper catalyzed aminobromination of alkene tethered thiohydroximic acids is described, providing a rapid approach to unnatural thiazoline scaffolds not readily available via existing methods. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2014 journal article

Synthesis of Thiohydroxamic Acids and Thiohydroximic Acid Derivatives

JOURNAL OF ORGANIC CHEMISTRY, 79(5), 2321–2330.

By: B. Lemercier n & J. Pierce n

TL;DR: An improved and expanded preparation of thiohydroxamic acids is reported along with a one-pot conversion of these compounds to novel thioHydroximic acid derivatives that serve as potentially useful building blocks for organic synthesis. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2012 journal article

Redesign of Glycopeptide Antibiotics: Back to the Future

ACS Chemical Biology, 7(5), 797–804.

By: R. James*, J. Pierce*, A. Okano*, J. Xie* & D. Boger*

MeSH headings : Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / pharmacology; Drug Design; Enterococcus / drug effects; Glycopeptides / chemistry; Glycopeptides / pharmacology; Gram-Positive Bacterial Infections / drug therapy; Humans; Methicillin Resistance; Models, Molecular; Staphylococcal Infections / drug therapy; Staphylococcus aureus / drug effects; Vancomycin / analogs & derivatives; Vancomycin / pharmacology; Vancomycin Resistance
TL;DR: Recent efforts to redesign glycopeptide antibiotics for the treatment of resistant microbial infections, including VRE and VRSA, are considered and their future potential for providing an even more powerful class of antibiotics that are even less prone to bacterial resistance is examined. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: August 28, 2020

2012 journal article

Silver(I)-Promoted Conversion of Thioamides to Amidines: Divergent Synthesis of a Key Series of Vancomycin Aglycon Residue 4 Amidines That Clarify Binding Behavior to Model Ligands

Journal of the American Chemical Society, 134(21), 8790–8793.

By: A. Okano*, R. James*, J. Pierce*, J. Xie* & D. Boger*

MeSH headings : Amidines / chemistry; Anti-Bacterial Agents / chemical synthesis; Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / metabolism; Anti-Bacterial Agents / pharmacology; Bacterial Proteins / metabolism; Catalysis; Chemistry Techniques, Synthetic; Drug Design; Drug Resistance, Bacterial / drug effects; Enterococcus faecalis / drug effects; Enterococcus faecalis / metabolism; Ligands; Peptidoglycan / chemistry; Peptidoglycan / pharmacology; Silver / chemistry; Thioamides / chemistry; Vancomycin / analogs & derivatives; Vancomycin / chemical synthesis; Vancomycin / chemistry; Vancomycin / metabolism; Vancomycin / pharmacology
TL;DR: Development of a general Ag(I)-promoted reaction for the conversion of thioamides to amidines is disclosed and this reaction was employed to prepare a key series of vancomycin aglycon residue 4 substituted amidines to clarify their interaction with model ligands of peptidoglycan precursors. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: December 22, 2020

2012 journal article

Synthesis of a library of tricyclic azepinoisoindolinones

Beilstein Journal of Organic Chemistry, 8, 1091–1097.

By: B. Miller, S. Mao, K. Rosenker, J. Pierce* & P. Wipf

author keywords: chemical diversity; epoxide aminolysis; hydrozirconation; isoindolinones; metathesis; N-acyliminium ion
TL;DR: The resulting library products provided selective hits among a large number of high-throughput screens reported in PubChem, thus illustrating the utility of the novel scaffold. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: December 24, 2020

2012 journal article

Total Synthesis of [Ψ[C(═S)NH]Tpg4]Vancomycin Aglycon, [Ψ[C(═NH)NH]Tpg4]Vancomycin Aglycon, and Related Key Compounds: Reengineering Vancomycin for Dual d-Ala-d-Ala and d-Ala-d-Lac Binding

Journal of the American Chemical Society, 134(2), 1284–1297.

By: J. Xie*, A. Okano*, J. Pierce*, R. James*, S. Stamm*, C. Crane*, D. Boger*

MeSH headings : Amino Acid Sequence; Anti-Bacterial Agents / chemical synthesis; Drug Resistance, Bacterial; Models, Molecular; Molecular Structure; Peptidoglycan / chemistry; Protein Binding; Vancomycin / analogs & derivatives; Vancomycin / chemical synthesis
TL;DR: The total synthesis of 7 and 8 and its unique AgOAc-promoted single-step conversion to [Ψ[C(═NH)NH]Tpg(4)]vancomycin aglycon and its related key synthetic compounds containing the core residue 4 amidine and thioamide modifications are reported, charting a rational approach forward in the development of antibiotics for the treatment of vancomYcin-resistant bacterial infections. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: December 22, 2020

2011 journal article

A Redesigned Vancomycin Engineered for Dual d-Ala-d-Ala and d-Ala-d-Lac Binding Exhibits Potent Antimicrobial Activity Against Vancomycin-Resistant Bacteria

Journal of the American Chemical Society, 133(35), 13946–13949.

By: J. Xie*, J. Pierce*, R. James*, A. Okano* & D. Boger*

MeSH headings : Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / metabolism; Bacteria / metabolism; Binding Sites; Cell Wall / metabolism; Dipeptides / metabolism; Peptidoglycan / metabolism; Vancomycin / chemistry; Vancomycin / metabolism; Vancomycin Resistance
TL;DR: A complementary single atom Exchange in the vancomycin core structure to counter the single atom exchange in the cell wall precursors of resistant bacteria (NH → O) reinstates potent antimicrobial activity and charts a rational path forward for the development of antibiotics for the treatment of vancomYcin-resistant bacterial infections. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: December 22, 2020

2011 journal article

Large-Scale Asymmetric Synthesis of the Bioprotective Agent JP4-039 and Analogs

Organic Letters, 13(9), 2318–2321.

MeSH headings : Amines / chemistry; Esters / chemistry; Models, Molecular; Molecular Structure; Nitrogen Oxides / chemical synthesis; Stereoisomerism
TL;DR: JP4-039 is a novel nitroxide conjugate capable of crossing lipid bilayer membranes and scavenging reactive oxygen species (ROS) and an efficient and scalable one-pot hydrozirconation-transmetalation-imine addition methodology has been developed for its asymmetric preparation. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: August 28, 2020

2010 journal article

Synthesis and Evaluation of Selected Key Methyl Ether Derivatives of Vancomycin Aglycon

Journal of Medicinal Chemistry, 53(19), 7229–7235.

By: C. Crane*, J. Pierce*, S. Leung*, J. Tirado-Rives*, W. Jorgensen* & D. Boger*

MeSH headings : Anti-Bacterial Agents / chemical synthesis; Anti-Bacterial Agents / pharmacology; Drug Resistance, Bacterial; Enterococcus faecalis / drug effects; Hydrophobic and Hydrophilic Interactions; Methyl Ethers / chemical synthesis; Methyl Ethers / pharmacology; Microbial Sensitivity Tests; Peptidoglycan / chemistry; Staphylococcus aureus / drug effects; Stereoisomerism; Structure-Activity Relationship; Thermodynamics; Vancomycin / analogs & derivatives; Vancomycin / chemical synthesis; Vancomycin / pharmacology
TL;DR: In these studies, methodology for selective derivatization of the A-, B-, and D-ring was developed that defines the relative reactivity of the four phenols of vancomycin aglycon, providing a foundation for future efforts for site-directed modification of the vancomYcin Aglycon core. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: August 28, 2020

2009 journal article

The Mitochondria-Targeted Nitroxide JP4-039 Augments Potentially Lethal Irradiation Damage Repair

In Vivo, 23(5), 717–726.

By: M. Rajagopalan, K. Gupta, M. Epperly, D. Franicola, X. Zhang, H. Wang, H. Zhao, V. Tyurin ...

Source: NC State University Libraries
Added: February 5, 2021

2008 journal article

Synthesis of Hydroxylated Bicyclic Amino Acids from l-Tyrosine: Octahydro-1 H-indole Carboxylates

The Journal of Organic Chemistry, 73(19), 7807–7810.

By: J. Pierce*, D. Kasi*, M. Fushimi*, A. Cuzzupe* & P. Wipf*

MeSH headings : Amino Acids / chemical synthesis; Amino Acids / chemistry; Bridged Bicyclo Compounds / chemical synthesis; Carboxylic Acids / chemistry; Hydroxylation; Indoles / chemistry; Stereoisomerism; Tyrosine / chemistry
TL;DR: A stereoselective approach to polyhydroxylated L-Choi derivatives has been developed and the oxidative cyclization of L-tyrosine was optimized to avoid partial racemization and to allow a more efficient scale-up. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: December 22, 2020

2008 journal article

The Mitochondrial Targeted GS-Nitroxide JP4-039 is Radioprotective In Vitro and In Vivo

International Journal of Radiation Oncology*Biology*Physics, 72(1), S82.

By: M. Epperly*, J. Pierce*, T. Dixon*, D. Franicola*, P. Wipf* & J. Greenberger*

Sources: Crossref, ORCID
Added: August 28, 2020

2007 journal article

Synthesis of functionalized isoindolinones: Addition of in situ generated organoalanes to acyliminium ions

Journal of Organometallic Chemistry, 692(21), 4618–4629.

By: J. Pierce*, D. Waller & P. Wipf

author keywords: isoindolinone; aluminum; zirconium; hydrozirconation; carbometallation; N-acyliminium ion
TL;DR: Addition of in situ generated di- or trisubstituted alkenylalanes to N-acyliminium ions provides rapid access to functionalized isoindolinones and leads to tricyclic products. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: August 28, 2020

2006 journal article

Expedient Synthesis of the α-C-Glycoside Analogue of the Immunostimulant Galactosylceramide (KRN7000)

Organic Letters, 8(15), 3375–3378.

By: P. Wipf* & J. Pierce*

MeSH headings : Adjuvants, Immunologic / chemical synthesis; Adjuvants, Immunologic / pharmacology; Galactosylceramides / chemical synthesis; Galactosylceramides / pharmacology; Glycosides / chemical synthesis; Imines / chemistry; Molecular Structure; Stereoisomerism
TL;DR: Key reactions in a concise synthesis of an alpha-C-galactosylceramide analogue of KRN7000 include a diastereoselective alkenylalane addition to an N-tert-butanesulfinyl imine and the use of an epoxidation/carbamate ring opening sequence to install the aminodiol stereotriad. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: August 28, 2020

2005 journal article

Catalytic Reduction of Amides to Amines with Hydrosilanes Using a Triruthenium Carbonyl Cluster as the Catalyst​

Organic Syntheses, 82, 188.

By: Y. Motoyama, C. Itonaga, T. Ishida, M. Takasaki & H. Nagazhima

Ed(s): P. Wipf & J. Pierce

Sources: Crossref, ORCID
Added: December 24, 2020

2005 journal article

Lipase-Catalyzed Resolution of 4-Trimethylsilyl-3-Butyn-2-ol and Conversion of the (R)-Enantiomer to (R)-3-Butyn-2-yl Mesylate and (P)-1-Tributylstannyl-1,2-Butadiene

Organic Syntheses, 4, 43–55.

By: J. Marshall* & H. Chobanian*

Sources: Crossref, ORCID
Added: December 24, 2020

2005 journal article

Silver(I)-Catalyzed Addition of Zirconocenes to Glycal Epoxides. A New Synthesis of α-C-Glycosides

Organic Letters, 7(3), 483–485.

By: P. Wipf*, J. Pierce* & N. Zhuang*

MeSH headings : Catalysis; Epoxy Compounds / chemical synthesis; Glycosides / chemical synthesis; Indicators and Reagents; Molecular Conformation; Organometallic Compounds / chemistry; Silver / chemistry; Stereoisomerism; Zirconium / chemistry
Sources: Crossref, ORCID
Added: August 28, 2020

2005 journal article

Synthesis of Homoallylic Amines by Hydrozirconation−Imine Addition of Allenes

Organic Letters, 7(16), 3537–3540.

By: P. Wipf* & J. Pierce*

TL;DR: Hydrozirconation of allenes followed by in situ transmetalation to dialkylzinc leads to the formation of an allylic zinc species that, upon addition of aldimines to the reaction mixture, provides homoallylic amines in 64-85% yield. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: August 28, 2020

2003 journal article

Investigation of ligand loading and asymmetric amplification in CHAOx-catalyzed asymmetric diethylzinc additions

Tetrahedron: Asymmetry, 14(22), 3605–3611.

By: P. Wipf*, J. Pierce* & X. Wang*

UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Crossref, ORCID
Added: December 24, 2020

Citation Index includes data from a number of different sources. If you have questions about the sources of data in the Citation Index or need a set of data which is free to re-distribute, please contact us.

Certain data included herein are derived from the Web of Science© and InCites© (2024) of Clarivate Analytics. All rights reserved. You may not copy or re-distribute this material in whole or in part without the prior written consent of Clarivate Analytics.