Abstract
This paper describes a novel approach for the introduction of a C-1 hydroxyl on the decalin ring system, starting from (-)-carvone. Utilizing the substrate-controlled Mukaiyama aldol reaction and alkaline cyclization as key steps, the C-1 oxygenated decalin eudesmane skeleton 2' and its four isomers were synthesized efficiently. Furthermore, X-ray structural analysis showed that the claimed structure for the natural product is incorrect.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Biological Factors / chemical synthesis
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Biological Factors / chemistry
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Cyclization
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Cyclohexane Monoterpenes
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Isomerism
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Models, Molecular
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Molecular Structure
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Monoterpenes
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Naphthalenes / chemistry*
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Sesquiterpenes / chemical synthesis*
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Sesquiterpenes / chemistry*
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Sesquiterpenes, Eudesmane / chemical synthesis*
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Sesquiterpenes, Eudesmane / chemistry*
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Terpenes / chemistry
Substances
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1,6-dihydroxyeudesm-3-ene
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Biological Factors
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Cyclohexane Monoterpenes
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Monoterpenes
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Naphthalenes
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Sesquiterpenes
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Sesquiterpenes, Eudesmane
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Terpenes
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carvone
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decalin