title: Chemoenzymatic synthesis of isogalactofagomine.
abstract: A new chemoenzymatic synthesis of optically pure isogalactofagomine 2 starting from achiral starting materials is presented. Dimethyl 4-hydroxypyridine-3,5-dicarboxylate (7) was synthesized and converted to the corresponding saturated piperidine 8. Then the key step of the synthesis was carried out: Lipase M catalyzed hydrolysis of the prochiral diester 8 to cause formation of an asymmetric monoacid with at least 98% enantiomeric excess. Reduction of the acid, saponification of the remaining ester, and radical iododecarboxylation gave an iodide that after substitution with silver trifluoroacetate and hydrolysis gave 2.
authors.affiliation: Department of Chemistry, University of Aarhus, DK-8000 Aarhus, Denmark.
authors.forename: X
authors.initials: X
authors.lastname: Liang
authors.forename: A
authors.initials: A
authors.lastname: Lohse
authors.forename: M
authors.initials: M
authors.lastname: Bols
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D007202:Indicators and Reagents; D008049:Lipase; D009682:Magnetic Resonance Spectroscopy; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors*
chemical_list: D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D010880:Piperidines; C416964:isogalactofagomine; D008049:Lipase; D001616:beta-Galactosidase; D005690:Galactose