Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: application to the synthesis of (-)-sedamine.
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.
Zheng
Guangrong
G
College of Pharmacy, University of Kentucky, Lexington, Kentucky 40536-0082, USA.
Dwoskin
Linda P
LP
Crooks
Peter A
PA
D000470:Alkaloids / Q000138:chemical synthesis*; D008120:Lobeline / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D010880:Piperidines; C459239:sedamine; D008120:Lobeline