Total synthesis of (-)-bitungolide F

J Org Chem. 2009 Apr 3;74(7):2743-9. doi: 10.1021/jo9000146.

Abstract

An efficient total synthesis of (-)-bitungolide F (6) in 17 steps and 20.1% yield is described herein. Key steps involve a Myers asymmetric alkylation to introduce the C6 methyl with proper stereochemistry, a Claisen-like cyclization to construct the alpha,beta-unsaturated delta-lactone and a Julia-Kocienski olefination to assemble the conjugated diene moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis
  • Alcohols / chemistry
  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Cyclization
  • Iodides / chemical synthesis
  • Iodides / chemistry
  • Molecular Structure
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry

Substances

  • Alcohols
  • Alkenes
  • Iodides
  • Pyrones
  • bitungolide F