title: Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: application to the synthesis of (-)-sedamine.
abstract: Alkyl chloroformates induced indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline is described. This strategy was applied to the conversion of (-)-lobeline to (-)-sedamine in high overall yield.
authors.affiliation: College of Pharmacy, University of Kentucky, Lexington, Kentucky 40536-0082, USA.
authors.forename: Guangrong
authors.initials: G
authors.lastname: Zheng
authors.forename: Linda P
authors.initials: LP
authors.lastname: Dwoskin
authors.forename: Peter A
authors.initials: PA
authors.lastname: Crooks
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D008120:Lobeline / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D010880:Piperidines; C459239:sedamine; D008120:Lobeline