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

被引：9

作者：

Fukaya, Keisuke ^{[1
]}

Yamaguchi, Yu ^{[1
]}

Watanabe, Ami ^{[1
]}

Yamamoto, Hiroaki ^{[1
]}

Sugai, Tomoya ^{[1
]}

Sugai, Takeshi ^{[2
]}

Sato, Takaaki ^{[1
]}

Chida, Noritaka ^{[1
]}

机构：

[1] Keio Univ, Dept Appl Chem, 3-14-1 Hiyoshi, Yokohama, Kanagawa 2238522, Japan

[2] Keio Univ, Dept Pharmaceut Sci, Tokyo, Japan

来源：

JOURNAL OF ANTIBIOTICS | 2016年 / 69卷 / 04期

基金：

日本学术振兴会;

关键词：

FORMAL TOTAL-SYNTHESIS; AQUEOUS-MEDIA; TAXOL; ACID; ALDOL; INTERMEDIATE; COMPLETION; (-)-TAXOL; TAXANES;

D O I：

10.1038/ja.2016.6

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

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.

引用

页码：273 / 279

页数：7

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