Abstract
A concise, biomimetic synthesis of the antifungal and antispasmodic natural product (+)-davanone is described. The key stereoselective reactions are a Sharpless asymmetric epoxidation, a thiazolium-catalyzed esterification, and a palladium-mediated cyclization. All carbons are derived from isoprene units and no protecting groups are used, permitting an atom- and redox-economical synthesis.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Antifungal Agents / chemical synthesis*
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Antifungal Agents / chemistry
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Artemisia / chemistry
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Biological Products / chemical synthesis*
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Biological Products / chemistry
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Catalysis
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Cyclization
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Esterification
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Molecular Structure
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Oxidation-Reduction
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Palladium / chemistry
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Parasympatholytics / chemical synthesis*
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Parasympatholytics / chemistry
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Sesquiterpenes / chemical synthesis*
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Sesquiterpenes / chemistry
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Stereoisomerism
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Thiazoles / chemistry
Substances
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Antifungal Agents
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Biological Products
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Parasympatholytics
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Sesquiterpenes
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Thiazoles
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davanone
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Palladium