Directed Oxidative Cyclizations to C2- or C4-Positions of Indole: Efficient Construction of the Bicyclo[4.3.1]Decane Core of Welwitindolinones

被引:42
作者
Bhat, Vikram [1 ]
MacKay, James A. [1 ]
Rawal, Viresh H. [1 ]
机构
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
关键词
CHIROPTICAL PROPERTIES; FISCHERINDOLES; ISOTHIOCYANATE; HAPALINDOLES; ALKALOIDS; SKELETON;
D O I
10.1021/ol201122f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regiocontrolled oxidative cyclizations of 3-substituted indoles are described herein. Specifically, it is shown that the installation of a chloride at C2 alters the Inherent propensity for cyclization at the 2-position of indole so as to favor the 4-position, enabling the construction of the unique framework found In most welwitindolinone alkaloids. The chloride functions here as more than a blocking group, as it also provides ready access to the corresponding oxindole.
引用
收藏
页码:3214 / 3217
页数:4
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