Total syntheses of epothilones B and D

J Org Chem. 2000 Nov 3;65(22):7456-67. doi: 10.1021/jo0007480.

Abstract

Total syntheses of the microtubule stabilizing antitumor drugs epothilone B and D are described, starting from optically pure (S)-malic acid and methyl (R)-3-hydroxy-2-methylpropionate. The synthesis is highly convergent by coupling the three fragments C1-C6 (fragment D), C7-C10 (fragment C), and C11-C21 (fragment B). Key steps are two stereoselective Wittig type olefinations to generate the 12,13- and 16,17-double bonds, an enantioselective Mukaiyama aldol addition to synthesize fragment D, and a sulfone anion allyl iodide alkylation to connect fragments B and C. Finally fragment D was attached to the B + C fragment via aldol addition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Epothilones*
  • Epoxy Compounds / chemical synthesis*
  • Indicators and Reagents
  • Thiazoles / chemical synthesis*

Substances

  • Antineoplastic Agents, Phytogenic
  • Epothilones
  • Epoxy Compounds
  • Indicators and Reagents
  • Thiazoles
  • desoxyepothilone B