title: Concise asymmetric syntheses of (-)-lentiginosine and of its pyrrolizidinic analogue.
abstract: (-)-Lentiginosine and its pyrrolizidinic analogue have been prepared in a straightforward five-step sequence from a versatile chiral cis-alpha,beta-epoxyamine.
authors.affiliation: LSPCMIB, UMR 5068, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse, France.
authors.forename: Tahar
authors.initials: T
authors.lastname: Ayad
authors.forename: Yves
authors.initials: Y
authors.lastname: Génisson
authors.forename: Michel
authors.initials: M
authors.lastname: Baltas
authors.forename: Liliane
authors.initials: L
authors.lastname: Gorrichon
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D001234:Aspergillus niger / Q000201:enzymology; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D005087:Glucan 1,4-alpha-Glucosidase / Q000037:antagonists & inhibitors; D005960:Glucosides / Q000378:metabolism; D010084:Oxidation-Reduction; D011763:Pyrrolizidine Alkaloids / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D004791:Enzyme Inhibitors; D005960:Glucosides; D011763:Pyrrolizidine Alkaloids; C063984:lentiginosine; C019502:4-nitrophenyl alpha-glucoside; D005087:Glucan 1,4-alpha-Glucosidase