Total Synthesis of Kalimantacin A

Org Lett. 2020 Aug 21;22(16):6349-6353. doi: 10.1021/acs.orglett.0c02190. Epub 2020 Aug 10.

Abstract

The kalimantacins make up a family of hybrid polyketide-nonribosomal peptide-derived natural products that display potent and selective antibiotic activity against multidrug resistant strains of Staphylococcus aureus. Herein, we report the first total synthesis of kalimantacin A, in which three fragments are prepared and then united via Sonogashira and amide couplings. The enantioselective synthetic approach is convergent, unlocking routes to further kalimantacins and analogues for structure-activity relationship studies and clinical evaluation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Biological Products
  • Carbamates / chemical synthesis
  • Fatty Acids, Unsaturated / chemical synthesis
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Biological Products
  • Carbamates
  • Fatty Acids, Unsaturated
  • kalimantacin A