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

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• 作者：Vikram Bhat ; James A. MacKay ; Viresh H. Rawal
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：June 17, 2011
• 年：2011
• 卷：13
• 期：12
• 页码：3214-3217
• 全文大小：789K
• 年卷期：v.13,no.12(June 17, 2011)
• ISSN：1523-7052

文摘

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.