Abstract
The first asymmetric total synthesis of rumphellclovane E, a clovane-type sesquiterpenoid, has been accomplished in eight steps from commercially available (R)-carvone. Key elements of the synthesis include Rh-catalyzed cyclopropanation, iron-catalyzed intramolecular reductive aldol reaction, and SmI2-mediated chemo- and diastereoselective reduction of the cyclopentanone.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry
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Catalysis
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Cyclohexane Monoterpenes / chemical synthesis*
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Cyclohexane Monoterpenes / chemistry
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Cyclopentanes
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Molecular Structure
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Sesquiterpenes / chemical synthesis*
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Sesquiterpenes / chemistry
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Stereoisomerism
Substances
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Aldehydes
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Cyclohexane Monoterpenes
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Cyclopentanes
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Sesquiterpenes
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cyclopentanone
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carvone
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3-hydroxybutanal