%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