This proposed project will focus on the development of a new method for stereoselective synthesis of alpha-2,3-unsaturated-O-glycosides directly from glycal trichoroacetimidates. This approach relies only on the nature of the catalyst-glycal complexation to control the stereoselectivity at the anomeric center. Studies to elucidate the mechanism of this reaction will be undertaken. This method will be applied toward the total synthesis of vineomycin as well as 1,2-cis glycosides. The second aspect of this proposal is to develop an efficient method for the synthesis of alpha- and beta-glycosyl ureas via palladium(II)-catalyzed rearrangement of glycal trichloroacetimidates. Studies to further elucidate the nature of the catalysts as well as the mechanism of the rearrangement will be undertaken.
With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Hien Nguyen of the Department of Chemistry and Biochemistry at Montana State University to develop efficient methods for constructing biologically active carbohydrates. Carbohydrates are the most structurally diverse class of biomolecules in nature, and it is now established that their critical roles in a variety of biological systems depend on the specific interactions between oligosacharides and other macromolecules. The research on the area of glycosyl ureas has recently emerged with applications in the field of aminoglycoside antibiotics.
