Abstract
The synthesis of (+/-)-methoxyfumimycin, a potential new bacterial peptide deformylase (PDF) inhibitor, is reported. To generate the stereogenic fully substituted carbon, the key step is a 1,2-addition of a methyl Grignard reagent to a ketimine. The overall synthetic strategy involves a Dakin oxidation of a vanillin derivative, Friedel-Crafts acylation, Claisen rearrangement, lactonization, and rhodium-catalyzed olefin isomerization.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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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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Benzaldehydes / chemistry*
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Benzofurans / chemical synthesis*
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Benzofurans / chemistry
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Catalysis
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Imines / chemical synthesis*
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Imines / chemistry
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Nitriles / chemical synthesis*
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Nitriles / chemistry
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Rhodium / chemistry*
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Stereoisomerism
Substances
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Anti-Bacterial Agents
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Benzaldehydes
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Benzofurans
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Imines
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Nitriles
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fumimycin
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ketimine
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vanillin
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Rhodium