General approach to glycosidase inhibitors. Enantioselective synthesis of deoxymannojirimycin and swainsonine |
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| Authors: | Martín Rubén Murruzzu Caterina Pericàs Miquel A Riera Antoni |
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| Institution: | 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. |
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| Abstract: | 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. |
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