Abstract
[reaction: see text] Enantioselective deprotonation of 4-substituted cyclohexanones and highly stereoselective conjugate addition of higher order mixed cuprates were the key steps in a concise synthesis of fumagalone-related molecules. The origin of the (low) biological activity of the new compounds as compared to fumagalone is briefly discussed.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aminopeptidases / antagonists & inhibitors*
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Cyclohexanes
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Cyclohexanones / chemical synthesis*
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Cyclohexanones / chemistry
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Cyclohexanones / pharmacology
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology
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Epoxy Compounds / chemical synthesis*
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Epoxy Compounds / chemistry
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Epoxy Compounds / pharmacology
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Fatty Acids, Unsaturated / chemistry
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Metalloendopeptidases / antagonists & inhibitors*
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Molecular Conformation
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Sesquiterpenes
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Stereoisomerism
Substances
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Cyclohexanes
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Cyclohexanones
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Enzyme Inhibitors
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Epoxy Compounds
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Fatty Acids, Unsaturated
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Sesquiterpenes
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fumagalone
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fumagillin
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Aminopeptidases
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methionine aminopeptidase 2
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Metalloendopeptidases