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  • Title: Synthesis of a sulfonium ion analogue of the glycosidase inhibitor swainsonine.
    Author: Kumar NS, Pinto BM.
    Journal: J Org Chem; 2006 Feb 03; 71(3):1262-4. PubMed ID: 16438551.
    Abstract:
    The synthesis of a bicyclic sulfonium ion analogue of a naturally occurring indolizidine alkaloid, swainsonine, in which the bridgehead nitrogen atom is replaced by a sulfonium ion, has been achieved by a multistep synthesis starting from (2S,3S,4R)-2,3-dibenzyloxy-4-formaldehyde-thiolane. 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 provides a candidate with which to further probe the hypothesis that a sulfonium salt carrying a permanent positive charge would be an effective glycosidase inhibitor.
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