Enantioselective Total Synthesis of (+)-Psiguadial B

被引：123
|
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
收藏
页码：9803 / 9806
页数：4
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