De novo syntheses of cleistriosides and cleistetrosides by tin-mediated regioselective glycosylation

ORGN 678

Miaosheng Li, Protea Organics, 955 Hartman Run Road, Morgantown, WV 26507 and George A. O'Doherty, george.odoherty@mail.wvu.edu, C. Eugene Bennett Department of Chemistry, West Virginia University, 284 Prospect Street, 217 Clark Hall of Chemistry, WVU, Morgantown, WV 26506-6045.
A de novo approach to partially acetylated dodecanyl rhamnoside derivatives, Cleistriosides and Cleistetrosides, which were isolated from Cleistopholis patens and Cleistopholis glauca and have significant antibacterial activity in vitro, was developed. This approach features a tin-mediated, palladium catalyzed regioselective glycosylation. Thus, Cleistetroside-2 was synthesized in 23 steps (5.9% total yield) from 2-acetylfuran.