A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H

被引：36
|
作者：
Shockley, Samantha E. [1 ]
Holder, Jeffrey C. [1 ]
Stoltz, Brian M. [1 ]
机构：
[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 24期
关键词：
ASYMMETRIC CONJUGATE ADDITION; TAIWANIA-CRYPTOMERIOIDES; ARYLBORONIC ACIDS; THUJA-STANDISHII; EFFICIENT ROUTE; DITERPENES; (+/-)-DICHROANONE; BARK; (+/-)-TAIWANIAQUINOL-B; CONSTANTS;
D O I：
10.1021/ol5031537
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H is reported. The all-carbon quaternary stereocenter was constructed by asymmetric conjugate addition catalyzed by a palladium(II) (S)-tert-butylpyridinooxazoline complex. The unexpected formation of a [3.2.1] bicyclic intermediate required the identification of a new route. Analysis of the Hammett constants for para-substituted arenes enabled the rational design of a highly enantioselective conjugate addition substrate that led to the completion of the formal synthesis.
引用
收藏
页码：6362 / 6365
页数：4
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