Biomimetic Synthesis of a New Class of Bacterial Signaling Molecules

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• 作者：Jesse B. Davis ; J. Daniel Bailey ; Jason K. Sello
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：July 16, 2009
• 年：2009
• 卷：11
• 期：14
• 页码：2984-2987
• 全文大小：141K
• 年卷期：v.11,no.14(July 16, 2009)
• ISSN：1523-7052

文摘

The first synthesis of a newly discovered class of bacterial signaling molecules from Streptomyces coelicolor has been developed. These molecules, known as the methylenomycin furans (MMFs), trigger production of the antibiotic methylenomycin. The synthesis features a scandium triflate-catalyzed domino reaction of β-ketoesters and dihydroxyacetone yielding 2,3,4-substituted furans. The proposed reaction sequence (aldol reaction, cyclization, and dehydrative aromatization) may be reminiscent of the biosynthetic reaction in which dihydroxyacetone phosphate and a β-ketothioester are condensed by an enzyme.