%0 Generic %A Ok, Taedong %A Jeon, Aram %A Lee, Joohee %A Lim, Jung Hak %A Hong, Chang Seop %A Lee, Hee-Seung %D 2007 %T Enantiomerically Pure Synthesis of β-Substituted γ-Butyrolactones:  A Key Intermediate to Concise Synthesis of Pregabalin %U https://acs.figshare.com/articles/dataset/Enantiomerically_Pure_Synthesis_of_Substituted_Butyrolactones_A_Key_Intermediate_to_Concise_Synthesis_of_Pregabalin/2985703 %R 10.1021/jo0709605.s006 %2 https://acs.figshare.com/ndownloader/files/4686361 %K Enantiomerically Pure Synthesis %K Key Intermediate %K derivative %K bicyclic %K Concise Synthesis %K decarbethoxylation %K Pregabalin %K enantiomerically %K utility %K acid %K isobutyl %K Butyrolactone %K Substituted %K lactone %K method %K anticonvulsant drug %K nucleophilic cyclopropane ring opening %K Chiral %K lignan %K butyrolactone %K scalable %K compound %K intermediate %K configuration %K pregabalin %K aminobutyric %K neuropathic pain %K synthesis %K GABA %X 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. %I ACS Publications