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  • Title: Biomimetic synthesis of a new class of bacterial signaling molecules.
    Author: Davis JB, Bailey JD, Sello JK.
    Journal: Org Lett; 2009 Jul 16; 11(14):2984-7. PubMed ID: 19545145.
    Abstract:
    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 beta-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 beta-ketothioester are condensed by an enzyme.
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