Abstract
[structure: see text]. A stereocontrolled total synthesis of the polycyclic Stemona alkaloid, (-)-stemospironine (1) has been achieved. Key transformations include the use of a Staudinger reaction leading to the aza-Wittig ring closure of the perhydroazepine system. Formation of the vicinal pyrrolidine butyrolactone is described via the stereoselective intramolecular capture of an intermediate aziridinium salt.
Publication types
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Research Support, U.S. Gov't, Non-P.H.S.
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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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Alkaloids / chemistry
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Magnetic Resonance Spectroscopy
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Magnoliopsida / chemistry
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Polycyclic Compounds / chemical synthesis*
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Polycyclic Compounds / chemistry
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry
Substances
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Alkaloids
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Polycyclic Compounds
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Spiro Compounds
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stemospironine