Intramolecular pyridine activation-dearomatization reaction: highly stereoselective synthesis of polysubstituted indolizidines and quinolizidines.
An unprecedented intramolecular pyridine activation-asymmetric dearomatization reaction is described. This process produces 5-substituted indolizidines and 6-substituted quinolizidines in excellent yields and in a highly regio- and diastereoselective fashion. Formal syntheses of trans-indolizidine alkaloids are presented along with some preliminary results in the formation of C-5 quaternary centers.
Barbe
Guillaume
G
Département de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
Pelletier
Guillaume
G
Charette
André B
AB
D000470:Alkaloids / Q000737:chemistry*; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D054836:Indolizidines; D011725:Pyridines; D054837:Quinolizidines; C023666:pyridine