Bioinspired Synthesis of Platensimycin from Natural ent-Kaurenoic Acids

Org Lett. 2023 Jul 28;25(29):5401-5405. doi: 10.1021/acs.orglett.3c01470. Epub 2023 Jun 20.

Abstract

The biomimetic formal synthesis of the antibiotic platensimycin for the treatment of infection by multidrug-resistant bacteria was accomplished starting from either ent-kaurenoic acid or grandiflorenic acid, each of which is a natural compound available in multigram scale from its natural source. Apart from the natural origin of the selected precursors, the keys of the described approach are the long-distance functionalization of ent-kaurenoic acid at C11 and the efficient protocol for the A-ring degradation of the diterpene framework.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adamantane*
  • Aminobenzoates
  • Diterpenes* / metabolism

Substances

  • kaurenoic acid
  • platensimycin
  • Diterpenes
  • Adamantane
  • Aminobenzoates