Abstract
An efficient and highly stereoselective synthesis of cytotoxic 8-epipuupehedione (1b) was achieved starting from natural (-)-drimenol (6). The key step to obtain stereoselectivity was the simultaneous demethylation and oxidation of the dihydrobenzopyran methoxy derivatives 10a and 10b.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / isolation & purification*
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Antineoplastic Agents / pharmacology
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Cyclization
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Drug Screening Assays, Antitumor
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Molecular Structure
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Oxidation-Reduction
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Polycyclic Sesquiterpenes
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Porifera / chemistry
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Stereoisomerism
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Terpenes / chemistry
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Terpenes / isolation & purification*
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Terpenes / pharmacology
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Tumor Cells, Cultured / drug effects
Substances
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8-epipuupehedione
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Antineoplastic Agents
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Polycyclic Sesquiterpenes
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Terpenes
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drimenol