The asymmetric total synthesis of cinbotolide: a revision of the original structure

J Org Chem. 2014 Dec 5;79(23):11349-58. doi: 10.1021/jo501471m. Epub 2014 Nov 14.

Abstract

The structure 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (1) was assigned to a metabolite of Botrytis cinerea, but the spectra of several synthetic analogues had significant differences from that of 1. Examination of the constituents of a B. cinerea mutant that overproduces polyketides gave sufficient quantities of 1, now named cinbotolide, for chemical transformations. These led to a revised γ-butyrolactone structure for the metabolite. This structure has been confirmed by an asymmetric total synthesis, which also established its absolute configuration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / chemistry*
  • Macrolides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Polyketides / chemical synthesis
  • Polyketides / chemistry*
  • Stereoisomerism

Substances

  • Macrolides
  • Polyketides
  • cinbotolide
  • 4-Butyrolactone