Iminosugars, both naturally occurring and synthetic, have proven clinical applications and potential therapeutic applications in the treatment of many diseases including diabetes, viral infections, cancer and metabolic disorders. Iminosugars are polyhydroxylated alkaloids that mimic sugars often binding to and blocking enzymes involved in carbohydrate processing. The described work provides synthetic routes to polyhydroxylated pyrrolidine, pyrrolizidine, and indolizidine iminosugars. Each class of iminosugar is obtained by changing the amine used in the reductive amination reaction. As a result of the polyhydroxylation, each iminosugar structure has multiple stereoisomers. The syntheses start with commercially available sugars and takes advantage of the sugars’ stereochemistry transferring three of their stereocenters to the final iminosugars. The synthetic results for all eight stereoisomers of (+)-lentiginosine and 1,4-dideoxy-1,4-imino-D-arabinol (DAB) will be described.

Efficient pyrrolidine-containing iminosugar synthesis utilizing a one-pot reaction involving a ring-opening reductive elimination, a reductive aminination and a intramolecular nucleophilic substitution reaction

ACS Spring 2022

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