Total synthesis of gonytolides C and G, lachnone C, and formal synthesis of blennolide C and diversonol

Org Biomol Chem. 2014 Aug 14;12(30):5601-10. doi: 10.1039/c4ob00950a. Epub 2014 Jun 23.

Abstract

The first stereoselective total synthesis of gonytolide C, which is a monomeric unit of an innate immune promoter gonytolide A, has been accomplished from the aldol reaction between acetophenone derived from orcinol and butyrolactone containing α-keto ester followed by the excellent diastereoselective intramolecular cyclization. The first total synthesis of gonytolide G has been achieved by the oxidation of benzylic methyl in gonytolide C. Additionally, total synthesis of lachnone C and a formal synthesis of blennolide C and diversonol have been achieved by this synthetic method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • 4-Butyrolactone / chemistry
  • Chromones / chemical synthesis*
  • Chromones / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Proton Magnetic Resonance Spectroscopy
  • Stereoisomerism
  • Temperature
  • Time Factors
  • Xanthones / chemical synthesis*
  • Xanthones / chemistry

Substances

  • Chromones
  • Lactones
  • Xanthones
  • blennolide C
  • diversonol
  • lachnone C
  • 4-Butyrolactone