Abstract
[reaction: see text] An enantioselective total synthesis of (-)-stemonine (1) is reported via a convergent assembly of the acyclic precursor 2. Key transformations include a Staudinger-aza-Wittig reaction to form the central perhydroazepine ring system and an iodine-induced tandem cyclization to construct the pyrrolidino-butyrolactone framework.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alkaloids / chemical synthesis*
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Azepines / chemistry
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Cyclization
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Iodine / chemistry
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Lactones / chemical synthesis*
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Lactones / chemistry
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Molecular Structure
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Pyrrolidines / chemical synthesis*
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Pyrrolidines / chemistry
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Stemonaceae / chemistry*
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Stereoisomerism
Substances
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Alkaloids
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Azepines
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Lactones
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Pyrrolidines
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stemonine
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Iodine
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hexahydroazepine