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De Novo Asymmetric Syntheses Of Biologically Active Natural Product, Haibing Guo
De Novo Asymmetric Syntheses Of Biologically Active Natural Product, Haibing Guo
Graduate Theses, Dissertations, and Problem Reports
The enantioselective syntheses of daumone and four analogs have been achieved in 7 to 8 steps. This route relies upon a diasteroselective palladium catalyzed glycosylation reaction for the formation of the anomeric bond. The asymmetry of the sugar and aglycone portion of daumone were introduced by Noyori reduction of an acylfuran and a propargyl ketone. A highly diastereoselective epoxidation and reductive ring opening established the desired C-2 and C-4 stereochemistry of daumone.;A highly enantioselective and stereocontrolled approach to D-, L-swainsonine and 8, 8a-epi-D-swainsonine has been developed from achiral furan or furfural. A one-pot hydrogenolysis, followed by an intramolecular reductive amination …