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 language | English |
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Pages (from-to) | 7390-7393 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 72 |
Issue number | 19 |
DOIs | |
Publication status | Published - 2007 Sep 14 |
ASJC Scopus subject areas
- Organic Chemistry