Physical Sciences and Mathematics Commons^™

Synthesizing Polyhydroxylated Indolizidines From D-Glucopyranoside, Stephanie Bryson

SURE (Stonehill Undergraduate Research Experience)

The individual sugars that constitute more complex carbo-hydrates are joined together by glycosidic bonds. Glycosidase enzymes catalyze the hydrolysis of these glycosidic bonds. The action of glycosidases plays an important role in viral infections, cancer, and diabetes. Iminosugars are nitrogen containing sugar analogs that are known to inhibit glycosidase function. The main objective of this research is to synthesize four of the possible 32 stereoisomers of a tetrahydoxylated indolizidine iminosugar (Figure 1) starting from a commercially available D-glucopyranoside. After synthesizing pyrrolidine 6 (39.3%), a ring-closing metathesis was performed to generate the indolizidine 7. A ruthenium catalyzed dihydroxylation followed by acetylation …