Total Synthesis of (+)-Scholarisine A

An effective total synthesis and assignment of the absolute configuration of the architecturally challenging compound (+)-scholarisine A has been achieved via a 20-step sequence. Highlights include a reductive cyclization involving a nitrile and an epoxide, a modified Fischer indole protocol, a late...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-03, Vol.134 (9), p.4037-4040
Main Authors: Adams, Gregory L, Carroll, Patrick J, Smith, Amos B
Format: Article
Language:English
Subjects:
Crystallography, X-Ray
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Models, Molecular
Molecular Structure
Stereoisomerism
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Summary:An effective total synthesis and assignment of the absolute configuration of the architecturally challenging compound (+)-scholarisine A has been achieved via a 20-step sequence. Highlights include a reductive cyclization involving a nitrile and an epoxide, a modified Fischer indole protocol, a late-stage oxidative lactonization, and an intramolecular cyclization leading to the indolenine ring system of (+)-scholarisine A.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja211840k