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

Fengtian Xue; Wenxin Gu; Richard B. Silverman

doi:10.1021/ol902109t

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

Fengtian Xue, Wenxin Gu, Richard B. Silverman

Chemistry

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

2-(((3R,4R)-4-(Allyloxy)-1-benzylpyrrolidin-3-yl)methyl)-6-(2,5-dimethyl-1 H-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.

Original language	English (US)
Pages (from-to)	5194-5197
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	22
DOIs	https://doi.org/10.1021/ol902109t
State	Published - 2009

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Concise route to the chiral pyrrolidine core of selective inhibitors of neuronal nitric oxide",

abstract = "2-(((3R,4R)-4-(Allyloxy)-1-benzylpyrrolidin-3-yl)methyl)-6-(2,5-dimethyl-1 H-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.",

author = "Fengtian Xue and Wenxin Gu and Silverman, {Richard B.}",

year = "2009",

doi = "10.1021/ol902109t",

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T1 - Concise route to the chiral pyrrolidine core of selective inhibitors of neuronal nitric oxide

AU - Xue, Fengtian

AU - Gu, Wenxin

AU - Silverman, Richard B.

PY - 2009

Y1 - 2009

N2 - 2-(((3R,4R)-4-(Allyloxy)-1-benzylpyrrolidin-3-yl)methyl)-6-(2,5-dimethyl-1 H-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.

AB - 2-(((3R,4R)-4-(Allyloxy)-1-benzylpyrrolidin-3-yl)methyl)-6-(2,5-dimethyl-1 H-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.

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JO - Organic Letters

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

Abstract

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