title: Synthesis of thioswainsonine as a potential glycosidase inhibitor.
abstract: The synthesis of a bicyclic sulfonium-ion analogue of a naturally occurring glycosidase inhibitor, swainsonine, in which the bridgehead nitrogen atom is replaced by a sulfonium ion, has been achieved by a multi-step synthesis starting from 1,4-anhydro-2,3-di-O-benzyl-4-thio-D-lyxitol. The synthetic strategy relies on the intramolecular displacement of a leaving group on a pendant acyclic chain by a cyclic thioether. This bicyclic sulfonium salt will serve as a candidate to test the hypothesis that a sulfonium salt carrying a permanent positive charge would be an effective glycosidase inhibitor.
authors: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6.
authors: Nag S
authors: NS
authors: Kumar
authors: B Mario
authors: BM
authors: Pinto