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Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A

2012; American Chemical Society; Volume: 135; Issue: 1 Linguagem: Inglês

10.1021/ja3111626

1943-2984

Gregory L. Adams, Patrick J. Carroll, Amos B. Smith,

Oxidative Organic Chemistry Reactions

The planning and implementation of an enantioselective total synthesis of (+)-scholarisine A is presented. Key tactics employed include a novel cyclization, consisting of a nitrile reduction coupled with concomitant addition of the resultant amine to an epoxide; a modified Fischer indolization; an oxidative lactonization of a diol in the presence of an indole ring; and a late-stage cyclization to complete the caged ring scaffold. The development of a possible "retro-biosynthetic" approach to other members of the akuammiline alkaloid family is also described.