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Org Lett. 2009 Nov 19;11(22):5194-7. doi: 10.1021/ol902109t.

Concise route to the chiral pyrrolidine core of selective inhibitors of neuronal nitric oxide.

Author information

1
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, USA.

Abstract

2-(((3R,4R)-4-(Allyloxy)-1-benzylpyrrolidin-3-yl)methyl)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridine (2), a key intermediate for the preparation of novel neuronal nitric oxide synthase (nNOS) inhibitors, is synthesized using diisopropyl (R)-(+)-malate as the starting material. The key steps involve a Frater-Seebach diastereoselective alkylation and a fast intramolecular cyclization.

PMID:
19860389
PMCID:
PMC2783674
DOI:
10.1021/ol902109t
[Indexed for MEDLINE]
Free PMC Article
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