Enantiomerically pure synthesis of β-substituted γ- butyrolactones: A key intermediate to concise synthesis of pregabalin

Taedong Ok, Aram Jeon, Joohee Lee, Hak Lim Jung, Chang Seop Hong, Hee Seung Lee

Research output: Contribution to journalArticle

63 Citations (Scopus)

Abstract

(Chemical Equation Presented) Chiral β-substituted γ-butyrolactones are known to be important intermediates for many biologically active compounds such as γ-aminobutyric acid (GABA) derivatives and lignans. We have developed a general, convenient, and scalable synthetic method for enantiomerically pure β-substituted γ-butyrolactones, with either configuration, via nucleophilic cyclopropane ring opening of (1S,5R)- or (1R,5S)-bicyclic lactone followed by decarbethoxylation. The utility of our method was demonstrated by streamlined synthesis of pregabalin ((S)-3-isobutyl-γ-aminobutyric acid), an anticonvulsant drug for the treatment of peripheral neuropathic pain.

Original languageEnglish
Pages (from-to)7390-7393
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number19
DOIs
Publication statusPublished - 2007 Sep 14

ASJC Scopus subject areas

  • Organic Chemistry

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