Total synthesis of epothilone D: the nerol/macroaldolization approach

J Org Chem. 2013 Nov 1;78(21):10588-95. doi: 10.1021/jo401355r. Epub 2013 Oct 22.

Abstract

A highly convergent and stereocontrolled synthesis of epothilone D (4) is reported. Key features are a cheap and Z-selective synthesis of the northern half based on nerol and acetoacetate and chromium(II)-mediated Reformatsky reactions as a powerful tool for chemoselective asymmetric carbon-carbon bond formations, including an unusual stereospecific macroaldolization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Chromium / chemistry
  • Epothilones / chemical synthesis*
  • Epothilones / chemistry
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry

Substances

  • Aldehydes
  • Epothilones
  • Macrolides
  • Chromium
  • desoxyepothilone B