Enantioselective syntheses of both enantiomers of noranabasamine.
Both the R and S enantiomers of the amphibian alkaloid noranabasamine were prepared in >30% overall yield with 80% ee and 86% ee, respectively. An enantioselective iridium-catalyzed N-heterocyclization reaction with either (R)- or (S)-1-phenylethylamine and 1-(5-methoxypyridin-3-yl)-1,5-pentanediol was employed to generate the 2-(pyridin-3-yl)-piperidine ring system in 69-72% yield.
Miao
Lei
L
Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, USA.
Dimaggio
Stassi C
SC
Shu
Hong
H
Trudell
Mark L
ML