title: Deoxygenative olefination reaction as the key step in the syntheses of deoxy and iminosugars.
abstract: Just a spoonful of sugar! A new synthetic strategy involving the use of a deoxygenative olefination reaction as the key step was developed for the preparation of deoxy and iminosugars in their optically active form (see scheme). This strategy has been proven successful by the use of a pentose, hexose, heptose, and disaccharide as the starting materials. Furthermore, it was applied in a formal total synthesis of iminosugar (-)-1-deoxy-L-fuconojirimycin, which can inhibit α-L-fucosidase.
authors.affiliation: Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 30013, ROC.
authors.forename: Yung
authors.initials: Y
authors.lastname: Chang Hsu
authors.forename: Jih Ru
authors.initials: JR
authors.lastname: Hwu
mesh_terms: D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000475:Alkenes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry; D002241:Carbohydrates; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors
chemical_list: D000475:Alkenes; D001555:Benzene Derivatives; D002241:Carbohydrates; D050111:Imino Sugars; D013402:Sugar Alcohols; C524146:benzyne; D017485:1-Deoxynojirimycin; C062662:deoxyfuconojirimycin; D005644:alpha-L-Fucosidase