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

Fengtian Xue, Wenxin Gu, Richard B. Silverman

Research output: Contribution to journalArticlepeer-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 languageEnglish (US)
Pages (from-to)5194-5197
Number of pages4
JournalOrganic Letters
Volume11
Issue number22
DOIs
StatePublished - 2009

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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