Rearrangement of O-cinnamoyltaxicin I to a novel C-13 spiro-taxane

J Nat Prod. 2000 Feb;63(2):179-81. doi: 10.1021/np990206h.

Abstract

During the large-scale synthesis of an O-cinnamoyltaxicin I acetonide, an intermediate for the semisynthesis of 7-deoxypaclitaxel derivatives, side-product 3 was formed via a vinylogous retro-aldol reaction and a long-range hydride shift from O-cinnamoyltaxicin I (1) under alkaline reaction conditions. Compound 3 has two hemi-acetal bridges at C-1,C-9 and C-10,C-13. Compound 4 was formed from side-product 3 under acidic reaction conditions and is the first C-13 spiro-taxane described in the literature. This spiro-taxane has two acetal bridges between C-1, C-13 and C-10,C-13.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Chromatography, High Pressure Liquid
  • Magnetic Resonance Spectroscopy
  • Paclitaxel / chemical synthesis*
  • Paclitaxel / chemistry
  • Plants, Medicinal / chemistry*

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Paclitaxel