Enantioselective Total Synthesis of (+)-Psiguadial B

被引：124

作者：

Chapman, Lauren M. ^{[1
]}

Beck, Jordan C. ^{[1
]}

Wu, Linglin ^{[1
]}

Reisman, Sarah E. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 31期

关键词：

CATALYTIC ASYMMETRIC-SYNTHESIS; ALPHA-AMINO-ACIDS; C-H BONDS; CONJUGATE ADDITION; BIOMIMETIC SYNTHESIS; QUATERNARY CENTERS; NATURAL-PRODUCTS; C(SP(3))-H BONDS; PSIDIUM-GUA[!text type='JAVA']JAVA[!/text; HIGHER-ORDER;

D O I：

10.1021/jacs.6b07229

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective total synthesis of the cytotoxic natural product (+)-psiguadial B is reported. Key features of the synthesis include (1) the enantioselective preparation of a key cyclobutane intermediate by a tandem Wolff rearrangement/asymmetric ketene addition, (2) a directed C(sp(3))-H alkenylation reaction to strategically forge the Cl-C2 bond, and (3) a ring-closing metathesis to build the bridging bicyclo[4.3.1]decane terpene framework.

引用

页码：9803 / 9806

页数：4

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