Total Synthesis of Violaceoid A and (-)- and (+)-Violaceoid B

被引：7

作者：

Murata, Takatsugu ^{[1
]}

Kuboki, Teppei ^{[1
]}

Ishikawa, Ryo ^{[1
]}

Saito, Takahiro ^{[1
]}

Taguchi, Shotaro ^{[1
]}

Takeuchi, Kazuma ^{[1
]}

Hatano, Emiko ^{[1
]}

Shimonaka, Motoyuki ^{[2
]}

Shiina, Isamu ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, 1-3 Kagurazaka, Tokyo 1628601, Japan

[2] Tokyo Univ Sci, Fac Sci, Dept Chem, Shinjuku Ku, 1-3 Kagurazaka, Tokyo 1628601, Japan

来源：

JOURNAL OF NATURAL PRODUCTS | 2018年 / 81卷 / 11期

关键词：

SECONDARY BENZYLIC ALCOHOLS; FREE CARBOXYLIC-ACIDS; KINETIC RESOLUTION; ASYMMETRIC ESTERIFICATION; ANHYDRIDE; DERIVATIVES;

D O I：

10.1021/acs.jnatprod.8b00215

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

The first total synthesis of violaceoid A, a cytotoxic agent, and the asymmetric total synthesis of (-)- and (+)-violaceoid B are reported. The precursor was accessed by desymmetrization of a substituted quinol moiety, and the racemic secondary alcohol was kinetically resolved using a chiral nucleophilic catalyst. The asymmetric synthesis of (-)- and (+)-violaceoid B elucidated the absolute configuration of the naturally occurring violaceoid B. Synthetic violaceoid A inhibited the growth of human breast cancer cell lines MCF-7 and Hs 578T at concentrations of less than 100 mu M, while (S)- and (R)-violaceoid B were inactive.

引用

页码：2364 / 2370

页数：7

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