Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 48, Pages 14432-14436Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507861
Keywords
glycosylation; natural products; oxidation; sulfur; synthetic methods
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Funding
- National Natural Science Foundation of China [21272082, 21402055, 21472054]
- State Key Laboratory of Bio-organic and Natural Products Chemistry [SKLBNPC13425]
- Natural Science Funds of Hubei Province for Distinguished Young Scholars [2015CFA035]
- Specialized Research Fund for the Doctoral Program of Higher Education [20120142120092]
- Thousand Talents Program Young Investigator Award
- Huazhong University of Science and Technology [2014ZZGH015]
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Latent O-glycosides, 2-(2propylthiol) benzyl (PTB) glycosides, were converted into the corresponding active glycosyl donors, 2-(2-propylsulfinyl) benzyl (PSB) glycosides, by a simple and efficient oxidation. Treatment of the PSB donor and various acceptors with triflic anhydride provided the desired glycosides in good to excellent yields. The leaving group, which was activated by an interrupted Pummerer reaction, can be recycled (PS-BOH) and regenerated as the precursor (PTB-OH). A natural hepatoprotective glycoside, leonoside F, was efficiently synthesized in a convergent [3+1] manner with this newly developed method. The present total synthesis also led to a structural revision of this phenylethanoid glycoside.
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