Abstract
Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (±)-naphthacemycin A9, and (±)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure-activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Biphenyl Compounds / chemical synthesis*
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Biphenyl Compounds / pharmacology*
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Drug Resistance, Microbial / drug effects*
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Gram-Positive Bacteria / drug effects*
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Naphthacenes / chemical synthesis*
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Naphthacenes / pharmacology*
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Polycyclic Aromatic Hydrocarbons / chemical synthesis*
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Polycyclic Aromatic Hydrocarbons / pharmacology*
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Polycyclic Compounds / chemical synthesis*
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Polycyclic Compounds / pharmacology*
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Structure-Activity Relationship
Substances
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Biphenyl Compounds
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Naphthacenes
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Polycyclic Aromatic Hydrocarbons
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Polycyclic Compounds
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fasamycin A
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naphthacemycin A9
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tetarimycin A