Stereoselective total synthesis of (-)-cleistenolide

J Org Chem. 2010 Aug 20;75(16):5754-6. doi: 10.1021/jo101059e.

Abstract

A facile stereoselective total synthesis of cleistenolide (1) from the natural chiral template d-arabinose has been achieved in eight steps and 49% overall yield, employing key steps including Wittig olefination, selective 1,3-trans-acetal formation, and modified Yamaguchi esterification.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Conformation
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Stereoisomerism

Substances

  • Pyrones
  • cleistenolide