Regiospecific Bromination of 3-Methylindoles with NBS and Its Application to the Concise Synthesis of Optically Active Unusual Tryptophans Present in Marine Cyclic …

R Liu, P Zhang, T Gan, JM Cook

Index: Liu, Ruiyan; Zhang, Puwen; Gan, Tong; Cook, James M. Journal of Organic Chemistry, 1997 , vol. 62, # 21 p. 7447 - 7456

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Citation Number: 73

Abstract

A regiospecific bromination of substituted 3-methylindoles at either the C (3) alkyl moiety or the C (2) position was achieved via a free radical bromination or electrophilic process, respectively. The regiospecificity of the bromination could be controlled by variation of both the substituent and the N (1) protecting group on the indole ring. In addition, enantiospecific syntheses of 5-methoxytryptophan (20) and 5-hydroxy-6-chlorotryptophan (21c) as well as ...