TY - JOUR
T1 - Enantiomerically pure synthesis of β-substituted γ- butyrolactones
T2 - A key intermediate to concise synthesis of pregabalin
AU - Ok, Taedong
AU - Jeon, Aram
AU - Lee, Joohee
AU - Jung, Hak Lim
AU - Chang, Seop Hong
AU - Lee, Hee Seung
PY - 2007/9/14
Y1 - 2007/9/14
N2 - (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.
AB - (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.
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U2 - 10.1021/jo0709605
DO - 10.1021/jo0709605
M3 - Article
C2 - 17715971
AN - SCOPUS:34548792285
VL - 72
SP - 7390
EP - 7393
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 19
ER -