General approach to glycosidase inhibitors. Enantioselective synthesis of deoxymannojirimycin and swainsonine.
[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.
Martín
Rubén
R
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.
Murruzzu
Caterina
C
Pericàs
Miquel A
MA
Riera
Antoni
A
D017485:1-Deoxynojirimycin / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D017026:Swainsonine / Q000138:chemical synthesis*
D004791:Enzyme Inhibitors; D017485:1-Deoxynojirimycin; D006026:Glycoside Hydrolases; D017026:Swainsonine