Iminosugars have been found to be useful and crucial as they can inhibit glycosidases, and therefore are important for medicinal purposes. The synthesis of different iminosugars could potentially lead to the treatment of diseases such as AIDS, HIV, and diabetes. The goal of this research is to synthesize two tetrahydroxylated pyrrolizidine stereoisomers from a commercially available methyl-a,D-galactopyranoside. The first part of the synthesis is the conversion of methyl-a,D-galactopyranoside to the selectively protected 6-deoxy-6-iodogalactopyranoside 6. Galactopyranoside 6 is then converted to divinylpyrrolidine 7 by a Zn mediated reductive elimination followed by a reductive amination of the resulting aldehyde with allyl amine and finally the spontaneous cyclization through a nucleophilic substitution reaction. A ruthenium catalyzed metathesis results in pyrrolizidine 8 followed by diydroxylation and deprotection should result in the desired tetrahydroxylated pyrrlolizidines 11 and 12.

The synthesis of tetrahydroxylated pyrrolizidines from methyl-a,D-glucopyranoside

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