title: Chemoenzymatic syntheses of (-)-1-deoxymannojirimycin (DMJ) and its naturally occurring 6-O-alpha-L-rhamnopyranosyl glycoside.
abstract: The naturally occurring sugar mimetic alkaloids 1-deoxymannojirimycin (DMJ, 1) and 6-O-alpha-L-rhamnopyranosyl-DMJ (2) have each been prepared in a completely stereoselective manner from the cis-1,2-dihydrocatechol 3, itself obtained in enantiomerically pure form by microbial oxidation of chlorobenzene.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. mgb@rsc.anu.edu.au
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.forename: Xinghua
authors.initials: X
authors.lastname: Ma
authors.forename: Naoki
authors.initials: N
authors.lastname: Asano
authors.forename: Kyoko
authors.initials: K
authors.lastname: Ikeda
authors.forename: John N
authors.initials: JN
authors.lastname: Lambert
mesh_terms: D017485:1-Deoxynojirimycin / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002396:Catechols / Q000737:chemistry; D002417:Cattle; D002722:Chlorobenzenes / Q000737:chemistry / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D010084:Oxidation-Reduction; D051381:Rats; D012210:Rhamnose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D002396:Catechols; D002722:Chlorobenzenes; D004791:Enzyme Inhibitors; D006027:Glycosides; D017485:1-Deoxynojirimycin; D006026:Glycoside Hydrolases; D012210:Rhamnose