Abstract
All stereoisomers of goniodiol were synthesized from yeast-reduction products. The C-6 chiral centers were converted from the chiral centers of the yeast-reduction products. Stereoselective conversion of the alkene, which had been prepared from the yeast-reduction product, to glycol constructed the C-7 and C-8 stereochemistry. (+)-Goniodiol and 7-epi-(+)-goniodiol showed the highest antibacterial activity (MIC, 3.1 mM) against Yersinia intermedia.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alcohols / chemistry
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Alkenes / chemistry
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology
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Furans / chemistry
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Microbial Sensitivity Tests
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Molecular Conformation
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Molecular Structure
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Optical Rotation
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Pyrones / chemistry*
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Stereoisomerism
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Structure-Activity Relationship
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Yeasts / chemistry*
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Yersinia / drug effects
Substances
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Alcohols
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Alkenes
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Anti-Bacterial Agents
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Furans
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Pyrones
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goniodiol