A formal total synthesis of taxol aided by an automated synthesizer

Chem Asian J. 2006 Sep 18;1(3):370-83. doi: 10.1002/asia.200600156.

Abstract

A 36-step synthesis was carried out in automated synthesizers to provide a synthetic key intermediate of taxol. A key step involved a microwave-assisted alkylation reaction to construct the ABC ring system from an AC precursor. Subsequent formation of the D ring afforded baccatin III, a well-known precursor of taxol.

MeSH terms

  • Alkaloids / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Automation
  • Centrifugation
  • Chemistry, Pharmaceutical / instrumentation*
  • Chemistry, Pharmaceutical / methods*
  • Computers
  • Filtration
  • Microwaves
  • Models, Chemical
  • Molecular Structure
  • Paclitaxel / chemical synthesis*
  • Paclitaxel / chemistry
  • Stereoisomerism
  • Taxoids / chemistry
  • Technology, Pharmaceutical / instrumentation*
  • Technology, Pharmaceutical / methods*
  • Temperature
  • Time Factors

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Taxoids
  • baccatin III
  • Paclitaxel