Concise asymmetric syntheses of (-)-lentiginosine and of its pyrrolizidinic analogue.
(-)-Lentiginosine and its pyrrolizidinic analogue have been prepared in a straightforward five-step sequence from a versatile chiral cis-alpha,beta-epoxyamine.
Ayad
Tahar
T
LSPCMIB, UMR 5068, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse, France.
Génisson
Yves
Y
Baltas
Michel
M
Gorrichon
Liliane
L
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
D000470:Alkaloids; D004791:Enzyme Inhibitors; D005960:Glucosides; D011763:Pyrrolizidine Alkaloids; C063984:lentiginosine; C019502:4-nitrophenyl alpha-glucoside; D005087:Glucan 1,4-alpha-Glucosidase