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Enantioselective syntheses of both enantiomers of noranabasamine.

ABSTRACT: 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.

SUBMITTER: Miao L

PROVIDER: S-EPMC2664076 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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Enantioselective syntheses of both enantiomers of noranabasamine.

Miao Lei L Dimaggio Stassi C SC Shu Hong H Trudell Mark L ML

Organic letters 20090401 7

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. ...[more]

PMID: 19320505

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