Carbohydrate analogues play an indispensible role in the study of glycan processing enzymes. These compounds have attracted attention as probes of enzyme mechanisms, as chemical tools for the elucidation of enzyme function and as potential pharmaceuticals. The development of organocatalytic aldol chemistry has fundamentally altered the way chemists approach the synthesis of carbohydrate analogues. In this thesis I highlight a novel strategy toward the synthesis of carbocyclic carbohydrate analogues which utilizes a proline-catalyzed aldol reaction and a metal-catalyzed carbocyclization as key steps. This strategy was successfully implemented in the synthesis of an ensemble of galactose and N-acetylgalactosamine analogues. Furthermore, I present preliminary results toward the biological evaluation of these compounds.
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