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Access to the akuammiline family of alkaloids: total synthesis of (+)-scholarisine A.

ABSTRACT: 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.

SUBMITTER: Adams GL 

PROVIDER: S-EPMC3557466 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Access to the akuammiline family of alkaloids: total synthesis of (+)-scholarisine A.

Adams Gregory L GL   Carroll Patrick J PJ   Smith Amos B AB  

Journal of the American Chemical Society 20121226 1

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 oth  ...[more]