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A Facile Synthesis of a (±)-2,3-Disubstituted Maleic Anhydride Segment of Tautomycin
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2001
Year
BiosynthesisEngineeringBiochemistryNatural SciencesFacile SynthesisDiversity-oriented SynthesisAntibiotic TautomycinOrganic ChemistryDiethyl MalonateSynthetic ChemistryPharmacologyMaleic Anhydride Segment-3-Methylmaleic AnhydrideBiomolecular EngineeringNatural Product Synthesis
A convenient method for construction of a (±)-2,3-disubstituted maleic anhydride segment of antibiotic tautomycin is reported. The key steps involved in the synthesis are chemoselective condensation of diethyl malonate with 2-(bromomethyl)-3-methylmaleic anhydride (3) and regioselective NBS-bromination of the maleic anhydride derivative 7.