Abstract
The enantioselective synthesis of (+)-17-norcharaciol is described. An uncatalyzed intramolecular carbonyl-ene reaction and a ring-closing metathesis were used as key C/C-connecting transformations to assemble the trans-bicyclo[10.3.0]pentadecane norditerpenoid core. We also report the evolution of our synthetic strategy toward the fully substituted characiol skeleton and the experiences from this venture.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Cyclopentanes / chemistry
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Diterpenes / chemical synthesis*
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Diterpenes / isolation & purification
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Diterpenes / pharmacology
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Esters / chemistry
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Euphorbia / chemistry*
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Humans
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Stereoisomerism
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Substrate Specificity
Substances
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15-acetyl-3-propionyl-17-norcharaciol
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Cyclopentanes
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Diterpenes
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Esters
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jatrophane