Journal
ORGANIC LETTERS
Volume 8, Issue 19, Pages 4339-4342Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol061683b
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Funding
- NIGMS NIH HHS [R01 GM063150-05, R01 GM063150, R01 GM063150-01A1, R01 GM063150-02, R01 GM063150-03, GM63150, R01 GM063150-04] Funding Source: Medline
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A convergent and stereocontrolled route to trisaccharide natural product digitoxin has been developed. The route is amenable to the preparation of both the digitoxigen mono- and bisdigitoxoside. This route featured the iterative application of the palladium-catalyzed glycosylation reaction, reductive 1,3-transposition, diastereoselective dihydroxylation, and regioselective protection. The natural product digitoxin was fashioned in 15 steps starting from digitoxigenin 2 and pyranone 8a or 18 steps from achiral acylfuran.
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