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

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 12期

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

页码：3214 / 3217

页数：4

共 44 条

[41]

Tsai AI, 2005, HETEROCYCLES, V65, P2381

[42] Electron Transfer Photoredox Catalysis: Intramolecular Radical Addition to Indoles and Pyrroles [J].