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 of the resulting syn- diols gave indolizidines 8 and 9. Research is currently underway using a transition-metal catalyst and the oxidant TBHP to produce anti-diol isomers, 10 and 11.
Bryson, Stephanie, "Synthesizing Polyhydroxylated Indolizidines from D-Glucopyranoside" (2019). SURE (Stonehill Undergraduate Research Experience). 2.