Abstract
The bicyclic gamma-ylidenetetronate motif found in several Stemona alkaloids was prepared in a stereoselective manner by addition of lithium methyl tetronate to an alkoxy oxonium ion formed from a lactone. The corresponding mixed alkyl ketal obtained was subjected to a Lewis acid-base-promoted dealkoxylation reaction to deliver the desired products.
Publication types
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Research Support, Non-U.S. Gov't
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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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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry
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Crystallography, X-Ray
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Molecular Conformation
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Molecular Structure
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Oxidation-Reduction
Substances
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Alkaloids
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Bridged Bicyclo Compounds, Heterocyclic