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    J Org Chem. 2005 Mar 18;70(6):2325-8.

    General approach to glycosidase inhibitors. Enantioselective synthesis of deoxymannojirimycin and swainsonine.

    Martín R, Murruzzu C, Pericàs MA, Riera A.

    Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Parc Científic de Barcelona, and Departament de Química Orgànica, Universitat de Barcelona, c/Josep Samitier, 1-5, 08028-Barcelona, Spain.

    [reaction: see text] Deoxymannojirimycin (2) and swainsonine (4) have been synthesized from each enantiomer of the same bicyclic carbamate precursor 7. The key intermediate was prepared by a simple and efficient three-step synthesis involving RCM of the diene 8, which in turn is easily accessible in any configuration from enantiomerically enriched 2,3-epoxy-4-penten-1-ol 9.

    PMID: 15760222 [PubMed - indexed for MEDLINE]

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