Abstract
A one-pot ring expansion/oxidation/elimination method has been developed in which beta-keto lactones are converted efficiently to alpha,beta-unsaturated-gamma-keto lactones. The reaction can be successfully applied to a variety of ring sizes. Alkene stereochemistry is dependent upon ring size and reaction conditions. The method was applied to the synthesis of (+)-patulolide A.
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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Alkenes / chemistry*
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Catalysis
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Cyclization
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Indicators and Reagents
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Ketones / chemistry*
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Lactones / chemical synthesis*
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Lactones / chemistry*
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Oxidation-Reduction
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Stereoisomerism
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Zinc / chemistry*
Substances
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Alkenes
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Indicators and Reagents
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Ketones
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Lactones
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patulolide B
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patulolide A
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Zinc