Selective fowler reductions: asymmetric total syntheses of isofagomine and other 1-azasugars from methyl nicotinate.
[figure: see text] An efficient, high-yielding strategy has been developed for the asymmetric synthesis of 1-N-iminosugars (1-azasugars), a new class of glycosidase inhibitors with promising biomedical applications. A highly regioselective procedure for the 1,2-reduction of substituted pyridines was employed to transform methyl nicotinate into several representative 1-azasugars.
Zhao
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Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
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D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D050112:Imino Pyranoses; D015394:Molecular Structure; D009539:Nicotinic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D001372:Aza Compounds; D004791:Enzyme Inhibitors; D050112:Imino Pyranoses; D009539:Nicotinic Acids; D010880:Piperidines; C098432:isofagomine; C008473:methyl nicotinate; D006026:Glycoside Hydrolases