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

7 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

Access to Document

10.1021/ol902109t

Fingerprint Dive into the research topics of 'Concise route to the chiral pyrrolidine core of selective inhibitors of neuronal nitric oxide'. Together they form a unique fingerprint.

Cite this

@article{b2363fcc9c654cf5bdf862e1a2f949a2,

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",

language = "English (US)",

volume = "11",

pages = "5194--5197",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=70749112280&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70749112280&partnerID=8YFLogxK

U2 - 10.1021/ol902109t

DO - 10.1021/ol902109t

M3 - Article

C2 - 19860389

AN - SCOPUS:70749112280

VL - 11

SP - 5194

EP - 5197

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 22

ER -