Oxidative and reductive transformations of epothilone A

Bioorg Med Chem Lett. 1998 Nov 3;8(21):3025-30. doi: 10.1016/S0960-894X(98)00545-9.

Abstract

The C7 hydroxy group of cytotoxic epothilone A was selectively oxidized using PDC. A selective oxidation of the C3 hydroxy group was accomplished with Me2S/(PhCO2)2 after in situ protection of C7-OH. Reduction of epothilone A or of a C5, C7 dioxo derivative with NaBH4 proceeded at the C5 carbonyl group. Oxidation and hydrogenation of the C16-C17 double bond proved to be difficult but it was easily cleaved with ozone and the resulting keto derivative was transformed to epothilone analogs with different side chains.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Epothilones*
  • Epoxy Compounds / chemical synthesis*
  • Fermentation
  • Oxidation-Reduction
  • Thiazoles / chemical synthesis*

Substances

  • Antineoplastic Agents
  • Epothilones
  • Epoxy Compounds
  • Thiazoles
  • epothilone A