The goal of this research was to synthesize the four possible stereoisomers of the polyhydroxylated indolizidine, octahydroindolizine-1,2,7,8-tetraol from D-glucopyranoside. Indolizidines are iminosugars which are sugar analogs that contain a nitrogen in the ring instead of an oxygen. Natural iminosugars such as Lentiginosene and Castanospermine are of interest because they are known inhibitors of glycosidases due to their similarity in structure of glycosidase substrates. Glycosidases are enzymes whose function is to break glycosidic bonds in complex sugars. This processing is important in diseases such as cancer, diabetes, and Gaucher disease. A hexahydroindolizine-1,2-diol was readily synthesized using previously known reactions.To synthesize the polyhydroxylated indolizidines, several dihydroxylation reactions were attempted on the olefin. The most successful dihydroxylation reaction used a ruthenium catalyst that complexes with the nitrogen in the ring to allow for stereochemically controlled dihydroxylation.  The diol products were acetylated to better stereochemically characterize the products.<br/>

Synthesis of polyhydroxylated indolizidine using ruthenium catalyzed dihydroxylation reaction

253rd National Meeting (2017)

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