The inhibition of glycosidases by iminosugars has the potential to treat a number of diseases including cancer, AIDS, and diabetes. One such sugar analog, Casuarine, is a naturally occurring pentahydroxylated pyrrolizidine that has been used in traditional medicine. The purpose of this research is to synthesize Casuarine as well as 7 of its 63 stereoisomers starting from D-glucose. The first part of the synthesis to form the intermediate glucopyranoside 4 as well as the required chiral allylic amine 13 were based off of previously developed chemistry. The chemistry to produce pyrrolizidine 18 was developed, which required the reductive opening of the iodoglucopyranoside with Zn followed by reductive amination of the resulting aldehyde with allylic amine 13. Two ring closing reactions, a metathesis and an intramolecular nucleophilic substitution, resulted in pyrrolizidine 18. Dihydroxylation of the double bond followed by hydrogenolysis results in Casuarine and its stereoisomers.

Synthesis of pentahydroxylated pyrrolizidine casuarine from D-glucopyranoside

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