Digital Commons Network^™

De Novo Asymmetric Synthesis Of Biologically Active Carbohydrate Natural Products And Related Sar Studies, Bulan Wu

Graduate Theses, Dissertations, and Problem Reports

The carbohydrate portion of natural products plays an important role in its biological activity, such as solubility, target binding, tissue targeting, and membrane transportation. Over the last fourteen years, Dr. O'Doherty's group has been developing de novo methodologies to build the desired carbohydrate functionality and stereochemistry within each sugar from simple achiral starting materials in stark contrast to the traditional carbohydrate approach using known sugar isomers as starting materials. The methodologies depend on a highly diasteroselective palladium-catalyzed glycosylation reaction to control the anomeric stereochemistry, and a highly enantioselective Noyori reduction to install the sugar absolute stereochemistry. Appropriate post-glycosylation transformations create …