Overturning Indolyne Regioselectivities and Synthesis of Indolactam V

被引：135

作者：

Bronner, Sarah M. ^{[1
]}

Goetz, Adam E. ^{[1
]}

Garg, Neil K. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 11期

关键词：

DIRECTED ORTHO-LITHIATION; 1,3-DIPOLAR CYCLOADDITION; DIELS-ALDER; ARYNE; REACTIVITY; SUBSTITUTION; BENZYNE; CHEMISTRY; DISCOVERY; ARYLATION;

D O I：

10.1021/ja200437g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the design and synthesis of an indolyne that displays a reversal in regioselectivity, in both nucleophilic addition and cycloaddition reactions, compared to typical 4,5-indolynes. Our approach utilizes simple computations to predict regioselectivity in reactions of unsymmetrical arynes. With this methodology, novel benzenoid-substituted indoles can be accessed with significant regiocontrol. Furthermore, the technology provides an unconventional tactic for the synthesis of C4-substituted indole alkaloids, as demonstrated by a synthesis of indolactam V.

引用

页码：3832 / 3835

页数：4

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