Nitrogen-containing sugar analogs classified as iminosugars, such as polyhydroxylated pyrrolizidines and indolizidines, are known for their ability to inhibit glycosidases. These enzymes are responsible for the breakdown of oligo- and polysaccharides to monosaccharides in the human body. This inhibition of glycosidases results in potential pharmaceutical and therapeutic uses for iminosugars. This research seeks to synthesize two (1 and 2) of the 32 potential stereoisomers of a tetrahydroxylated indolizidine from a commercially D-glucopyranoside 3. To date, two stereoisomers of precursor epoxides (4 and 5) have been synthesized in 2% and 5% yields. These epoxides will be hydrolytically opened, affording two hydroxyl groups in the anti-configuration of the desired tetrahydroxylated indolizidines. The final steps of the synthesis include deprotecting all hydroxyl groups to afford compounds 1 and 2.

Synthesis of tetrahydroxylated indolizidines from commercially available D-glucopyranoside

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