Reducing or eliminating organic solvent use in pharmaceutical manufacturing is perhaps the most effective way to reduce the environmental, health, and safety impacts of drug substance manufacturing. With this in...
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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