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A highly enantioselective and straightforward route to trisaccharide natural products digoxose and digitoxin has been developed. Key to this approach is the iterative application of the palladium-catalyzed glycosylation reaction, reductive 1,3-transposition, diastereoselective dihydroxylation, and regioselective protection. The first total synthesis of natural product digoxose was accomplished in 19 total steps from achiral 2-acylfuran, and digitoxin was fashioned in 15 steps starting from digitoxigenin 2 and pyranone 8beta. This flexible synthetic strategy also allows for the preparation of mono- and disaccharide analogues of digoxose and digitoxin.

De Novo Approach to 2-Deoxy-β-glycosides: Asymmetric Syntheses of Digoxose and Digitoxin1

De Novo Approach to 2-Deoxy-β-glycosides: Asymmetric Syntheses of Digoxose and Digitoxin¹