De novo asymmetric synthesis of antigen Bacillus anthracis tetrasaccharide

ORGN 917

Haibing Guo, haibingguojj@yahoo.com 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, Morgantown, WV 26506
The enantioselective synthesis of antigen Bacillus anthracis tetrasaccharide is developed in 22 steps starting from achiral acylfuran. This route relies upon an Achmatowicz rearrangement, a diastereoselective palladium-catalyzed glycosylation, Luche reductionn, and a dihydroxylation reaction. The asymmetry of tetrasaccharide is introduced by Noyori reduction of an acylfuran. Our current synthetic effort toward the tetrasaccharide will be presented.