The Enantiospecific, Stereospecific Total Synthesis of the Ring-A Oxygenated Sarpagine Indole Alkaloids (+)-Majvinine,(+)-10-Methoxyaffinisine, and (+)-N a- …

…, T Wang, J Flippen-Anderson, JM Cook

Index: Zhao, Shuo; Liao, Xuebin; Wang, Tao; Flippen-Anderson, Judith; Cook, James M. Journal of Organic Chemistry, 2003 , vol. 68, # 16 p. 6279 - 6295

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Citation Number: 42

Abstract

The first stereospecific, enantiospecific total synthesis of the ring-A oxygenated sarpagine indole alkaloids (+)-N a-methylsarpagine (8),(+)-majvinine (14), and (+)-10- methoxyaffinisine (49), as well as the first total synthesis of the Alstonia bisindole alkaloid macralstonidine (9), has been accomplished. This approach employed the Schöllkopf chiral auxiliary for the stereospecific construction of the desired d-(+)-tryptophan unit required for ...