Abstract
The first total synthesis of cristatic acid 1, an antibiotic endowed with considerable activity against Gram-positive bacteria, hemolytic properties, and significant cytotoxicity, is described. Key to success are the formation of its 2,4-disubstituted furan moiety via a palladium-catalyzed alkylation of vinylepoxide 10 derived from sulfonium salt 8 and the use of SEM ethers as the protecting groups for the phenolic OH functions.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Agaricales
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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 / chemical synthesis
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Furans / chemistry
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Furans / pharmacology
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Gram-Positive Bacteria / drug effects
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Indicators and Reagents
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Models, Molecular
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Molecular Conformation
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Salicylates / chemical synthesis
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Salicylates / chemistry
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Salicylates / pharmacology
Substances
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Anti-Bacterial Agents
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Furans
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Indicators and Reagents
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Salicylates
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cristatic acid