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

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 o...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2013-01, Vol.135 (1), p.519-528
Main Authors: Adams, Gregory L, Carroll, Patrick J, Smith, Amos B
Format: Article
Language:English
Subjects:
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Models, Molecular
Molecular Conformation
Stereoisomerism
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Description
Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja3111626