| Enantiomerically pure synthesis of beta-substituted gamma-butyrolactones: a key intermediate to concise synthesis of pregabalin. | |
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MedLine Citation:
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PMID: 17715971 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Chiral beta-substituted gamma-butyrolactones are known to be important intermediates for many biologically active compounds such as gamma-aminobutyric acid (GABA) derivatives and lignans. We have developed a general, convenient, and scalable synthetic method for enantiomerically pure beta-substituted gamma-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-gamma-aminobutyric acid), an anticonvulsant drug for the treatment of peripheral neuropathic pain. |
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Authors:
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Taedong Ok; Aram Jeon; Joohee Lee; Jung Hak Lim; Chang Seop Hong; Hee-Seung Lee |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2007-08-23 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Sep |
Date Detail:
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Created Date: 2007-09-07 Completed Date: 2007-10-16 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 7390-3 Citation Subset: IM |
Affiliation:
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Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejeon, Korea 305-701. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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4-Butyrolactone
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chemical synthesis*,
chemistry Anticonvulsants / chemical synthesis, chemistry Crystallography, X-Ray Stereoisomerism gamma-Aminobutyric Acid / analogs & derivatives*, chemical synthesis |
| Chemical | |
Reg. No./Substance:
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0/Anticonvulsants; 0/pregabalin; 56-12-2/gamma-Aminobutyric Acid; 96-48-0/4-Butyrolactone |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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