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

doi:10.1038/ja.2016.6

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 journal › Article › peer-review

9 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 language	English
Pages (from-to)	273-279
Number of pages	7
Journal	Journal of Antibiotics
Volume	69
Issue number	4
DOIs	https://doi.org/10.1038/ja.2016.6
Publication status	Published - 2016 Apr 1

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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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.",

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AU - Fukaya, Keisuke

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AU - Sugai, Takeshi

AU - Sato, Takaaki

AU - Chida, Noritaka

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

Abstract

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