| Abstract
| - A highly enantioselective and straightforward route to trisaccharide natural products digoxose and digitoxinhas been developed. Key to this approach is the iterative application of the palladium-catalyzedglycosylation reaction, reductive 1,3-transposition, diastereoselective dihydroxylation, and regioselectiveprotection. The first total synthesis of natural product digoxose was accomplished in 19 total steps fromachiral 2-acylfuran, and digitoxin was fashioned in 15 steps starting from digitoxigenin 2 and pyranone8β. This flexible synthetic strategy also allows for the preparation of mono- and disaccharide analoguesof digoxose and digitoxin.
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