De novo approach to 2-deoxy-beta-glycosides: asymmetric syntheses of digoxose and digitoxin
Maoquan Zhou1, George A O'Doherty
1Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Abstract:
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.
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