Synthesis of a novel C-10 spiro-epoxide of paclitaxel

Bioorg Med Chem Lett. 2001 Jul 9;11(13):1683-5. doi: 10.1016/s0960-894x(01)00280-3.

Abstract

New analogues of paclitaxel (1a, active constituent of Taxol) were synthesized containing an epoxide at the C-10 position. The introduction of the epoxide was carried out by selective removal of the C10-acetate followed by protection of the C2'- and C7-hydroxyl groups. After oxidation to yield a ketone at the C10-position, this intermediate was reacted with dimethylsulfonium ylide. Deprotection and further manipulations provide the C10-spiro epoxide of paclitaxel (1b) and the corresponding C7-MOM ether (1c).

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Colonic Neoplasms / pathology
  • Drug Screening Assays, Antitumor
  • Epoxy Compounds / chemical synthesis*
  • Female
  • Humans
  • Ovarian Neoplasms / pathology
  • Paclitaxel / analogs & derivatives*
  • Paclitaxel / chemistry
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Epoxy Compounds
  • Paclitaxel