SYNTHESIS OF C-GLYCOSIDES WITH METAL CATALYSTS

Stanford University, Stanford CA

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Abstract

C-linked glycosides are gaining more attention in the chemical community due to their novel structures and importance in carbohydrate and metabolic chemistry. Chemical synthesis of these targets is limited to several methodologies, few of which are convergent, one pot procedures. In this proposal, novel Ni and Pd catalyzed methodology has been proposed to prepare a variety of these biologically C-glycosides. These methods are based on well precedented organometallic reactions and will utilize a variety of mono- and bidentate phosphine ligands to control the chemistry. The synthetic methodology will be illustrated by the rapid, convergent synthesis of alpha-C- mannosyltryptophan, a naturally occurring amino acid in RNase2 from human erythrocytes.