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

J Org Chem. 2024 Dec 20;89(24):18729-18732. doi: 10.1021/acs.joc.4c02362. Epub 2024 Nov 27.

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.

MeSH terms

  • Anti-Bacterial Agents* / chemistry
  • Molecular Structure
  • Peptides / chemistry
  • Structure-Activity Relationship
  • Thiazoles* / chemistry

Substances

  • Anti-Bacterial Agents
  • Thiazoles
  • Peptides