Asymmetric syntheses of (-)-lentiginosine and an original pyrrolizidinic analogue thereof from a versatile epoxyamine intermediate.
Ready access to natural (-)-lentiginosine and its pyrrolizidinic analogue from a chiral vinylic epoxyamine in a straightforward five-step sequence is presented. Careful use of the RCM reaction on aminotriols and constitutes the key feature of the synthetic pathway. The alpha-amyloglucosidase inhibitory activities of the target compounds were evaluated and showed that the more easily accessible pyrrolizidinic analogue possesses an inhibitory activity quite similar to that of (-)-lentiginosine.
LSPCMIB,UMR 5068, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse, France.
Tahar
T
Ayad
Yves
Y
Génisson
Michel
M
Baltas
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D001234:Aspergillus niger / Q000201:enzymology; D004852:Epoxy Compounds / Q000737:chemistry*; D005087:Glucan 1,4-alpha-Glucosidase / Q000737:chemistry / Q000187:drug effects; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000470:Alkaloids; D000588:Amines; D004852:Epoxy Compounds; D011763:Pyrrolizidine Alkaloids; C063984:lentiginosine; D005087:Glucan 1,4-alpha-Glucosidase