Practical synthesis of the C-ring precursor of paclitaxel from 3-methoxytoluene

Keisuke Fukaya, Yu Yamaguchi, Ami Watanabe, Hiroaki Yamamoto, Tomoya Sugai, Takeshi Sugai, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The practical synthesis of the C-ring precursor of paclitaxel starting from 3-methoxytoluene is described. Lipase-catalyzed kinetic resolution of a substituted cyclohexane-1,2-diol, derived from 3-methoxytoluene in three steps, successfully afforded a desired enantiomer with >99% ee, which was transformed to a cyclohexenone. 1,4-Addition of a vinyl metal species, followed by Mukaiyama aldol reaction with formalin in the presence of a Lewis acid provided the known C-ring precursor of paclitaxel in a 10 g scale.

Original languageEnglish
Pages (from-to)273-279
Number of pages7
JournalJournal of Antibiotics
Volume69
Issue number4
DOIs
Publication statusPublished - 2016 Apr 1

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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