Stereoselective synthesis of 2,6-disubstituted 3-piperidinols: application to the expedient synthesis of (+)-julifloridine.
[reaction: see text] The asymmetric synthesis of 2,6-disubstituted 3-piperidinols having a 2,3-cis and 2,6-trans relative stereochemistry was accomplished in three steps using the following sequence: stereocontrolled nucleophilic addition of an organomagnesium reagent to a chiral pyridinium salt; monohydrogenation of the resulting 2-substituted 1,2-dihydropyridine; and a one-pot, highly diastereoselective epoxidation-nucleophilic addition with a heteroatom nucleophile or an organometallic reagent. This methodology was applied to the expedient asymmetric synthesis of (+)-julifloridine in four steps.
Lemire
Alexandre
A
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec H3C 3J7, Canada.
Charette
André B
AB
D000470:Alkaloids / Q000138:chemical synthesis*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*; D011726:Pyridinium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D010880:Piperidines; D011726:Pyridinium Compounds; C509192:julifloridine