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Journal Article

Total Synthesis of Cristatic Acid

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Gastner,  Thomas
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., & Gastner, T. (2000). Total Synthesis of Cristatic Acid. Organic Letters, 2(16), 2467-2470. doi:10.1021/ol0061236.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0024-4868-E
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.