IOOC Route to Substituted Chiral Pyrrolidines. Potential Glycosidase Inhibitors

Abstract

Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime−olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from d-serine, was about 1 order of potency more active than its enantiomer obtained from l-serine.