General approach to the total synthesis of 9-methoxy-substituted indole alkaloids: Synthesis of mitragynine, as well as 9-methoxygeissoschizol and 9-methoxy-N b- …

J Ma, W Yin, H Zhou, X Liao…

Index: Ma, Jun; Yin, Wenyuan; Zhou, Hao; Liao, Xuebin; Cook, James M. Journal of Organic Chemistry, 2009 , vol. 74, # 1 p. 264 - 273

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Citation Number: 53

Abstract

Herein, the full details of the synthesis of the 9-methoxy-substituted Corynanthe indole alkaloids mitragynine (1), 9-methoxygeissoschizol (3), and 9-methoxy-N b- methylgeissoschizol (4) are described. Initially, an efficient synthetic route to the optically active 4-methoxytryptophan ethyl ester 20 on a multigram scale was developed via a Mori− Ban− Hegedus indole synthesis. The ethyl ester of d-4-methoxytryptophan 20 was ...