Enantiomerically Pure Synthesis of -Substituted -Butyrolactones: A Key Intermediate to Concise Synthesis of Pregabalin

详细信息    查看全文

• 作者：Taedong Ok ; Aram Jeon ; Joohee Lee ; Jung Hak Lim ; Chang Seop Hong ; Hee-Seung Lee
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：September 14, 2007
• 年：2007
• 卷：72
• 期：19
• 页码：7390 - 7393
• 全文大小：118K
• 年卷期：v.72,no.19(September 14, 2007)
• ISSN：1520-6904

文摘

Chiral -substituted -butyrolactones are known to beimportant intermediates for many biologically active compounds such as -aminobutyric acid (GABA) derivatives andlignans. We have developed a general, convenient, andscalable synthetic method for enantiomerically pure -substituted -butyrolactones, with either configuration, vianucleophilic cyclopropane ring opening of (1S,5R)- or(1R,5S)-bicyclic lactone followed by decarbethoxylation. Theutility of our method was demonstrated by streamlinedsynthesis of pregabalin ((S)-3-isobutyl--aminobutyric acid),an anticonvulsant drug for the treatment of peripheralneuropathic pain.