Abstract
The first total synthesis of the monoamine oxidase inhibitors chaetoquadrins A-C has been accomplished. Key steps in the synthesis include an aromatic Claisen rearrangement, asymmetric boron aldol reaction and acid-mediated spiroketalization. Comparison of spectral data for the synthetic spiroketals confirmed the proposed structure for these natural products.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Ascomycota / chemistry
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Biological Products / chemical synthesis*
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Biological Products / chemistry
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Biological Products / pharmacology
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Heterocyclic Compounds, 4 or More Rings / pharmacology
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Lactones / chemical synthesis
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Lactones / chemistry
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Molecular Structure
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Monoamine Oxidase Inhibitors / chemical synthesis*
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Monoamine Oxidase Inhibitors / chemistry
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Monoamine Oxidase Inhibitors / pharmacology
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry
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Spiro Compounds / pharmacology
Substances
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Biological Products
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Heterocyclic Compounds, 4 or More Rings
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Lactones
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Monoamine Oxidase Inhibitors
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Spiro Compounds
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chaetoquadrin A
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chaetoquadrin B
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chaetoquadrin C