Abstract
The total synthesis of sculponeatin N, a bioactive polycyclic diterpene isolated from Isodon sculponeatus, is reported. Key features of the synthesis include diastereoselective Nazarov and ring-closing metathesis reactions, and a highly efficient formation of the bicyclo[3.2.1]octane ring system by a reductive radical cyclization.
Keywords:
isodon terpenes; natural products; reductive cyclization; ring-closing metathesis.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Bridged Bicyclo Compounds / chemistry
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Cell Line, Tumor
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Cell Survival / drug effects
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Cyclization
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Diterpenes / chemical synthesis
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Diterpenes / chemistry
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Free Radicals / chemistry
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Hep G2 Cells
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Humans
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Isodon / chemistry*
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Isodon / metabolism
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Stereoisomerism
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Terpenes / chemical synthesis*
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Terpenes / chemistry
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Terpenes / pharmacology
Substances
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Bridged Bicyclo Compounds
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Diterpenes
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Free Radicals
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Terpenes
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sculponeatin N