Diversity Oriented Routes to Thiopeptide Antibiotics: A Solution to the “Thiazole Problem”

The Goossen decarboxylative coupling reaction enables the union of thiazole-2-carboxylic acids with a 2-pyridyl triflate, leading to the formation of pyridine-thiazole clusters of the kind found in thiopeptide antibiotics. The method avoids problematic or technically challenging reaction sequences involving 2-thiazolyl organometallics, facilitating the investigation of the structure-activity relationship of the thiopeptides.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-11-27
DOI
https://doi.org/10.1021/acs.joc.4c02362
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Diversity Oriented Routes to Thiopeptide Antibiotics: A Solution to the “Thiazole Problem”

Morag Ferguson, Marco A. Ciufolini
The Journal of Organic Chemistry
Chemical Synthesis and Analysis
article

Diversity Oriented Routes to Thiopeptide Antibiotics: A Solution to the “Thiazole Problem”

Morag Ferguson, Marco A. Ciufolini
article en

Abstract

The Goossen decarboxylative coupling reaction enables the union of thiazole-2-carboxylic acids with a 2-pyridyl triflate, leading to the formation of pyridine-thiazole clusters of the kind found in thiopeptide antibiotics. The method avoids problematic or technically challenging reaction sequences involving 2-thiazolyl organometallics, facilitating the investigation of the structure-activity relationship of the thiopeptides.

The Journal of Organic ChemistryVol. 89(24)
University of British Columbia (CA)
Natural Sciences and Engineering Research Council of Canada
Zero hunger
Openalex Percentile: Top 81%
Chemical Synthesis and Analysis
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