Entry into 6-methoxy-D (+)-tryptophans. Stereospecific synthesis of 1-benzenesulfonyl-6-methoxy-D (+)-tryptophan ethyl ester

MS Allen, LK Hamaker, AJ La Loggia…

Index: Allen; Hamaker; La Loggia; Cook Synthetic Communications, 1992 , vol. 22, # 14 p. 2077 - 2102

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Citation Number: 70

Abstract

Abstract A strategy for the synthesis of optically active ring-A methoxylated indole alkaloids which employs the Moody azide/Schollkopf chiral auxiliary protocol has resulted in the successful preparation of 1-benzenesulfonyl-6-methoxy-D (+)-tryptophan ethyl ester 16. This amino ester is required for the synthesis of Alstonia bisindole alkaloids including macralstonine 2 via an enantiospecific Pictet-Spengler reaction.

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