Total syntheses of epothilones B and d

J Org Chem. 2004 Dec 24;69(26):9269-84. doi: 10.1021/jo048742o.

Abstract

A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12-C13, Wadsworth-Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection of acid 52, and macrolactonization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Epothilones / chemical synthesis*
  • Epothilones / chemistry
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Spectrophotometry, Infrared
  • Stereoisomerism

Substances

  • Epothilones
  • desoxyepothilone B
  • epothilone B