Chemoenzymatic synthesis of isogalactofagomine.
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.
Liang
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X
Department of Chemistry, University of Aarhus, DK-8000 Aarhus, Denmark.
Lohse
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A
Bols
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M
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*
D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D010880:Piperidines; C416964:isogalactofagomine; D008049:Lipase; D001616:beta-Galactosidase; D005690:Galactose