DC Field | Value | Language |
---|---|---|
dc.contributor.author | Ok, T | ko |
dc.contributor.author | Jeon, A | ko |
dc.contributor.author | Lee, J | ko |
dc.contributor.author | Lim, JH | ko |
dc.contributor.author | Hong, CS | ko |
dc.contributor.author | Lee, Hee-Seung | ko |
dc.date.accessioned | 2013-03-07T17:08:35Z | - |
dc.date.available | 2013-03-07T17:08:35Z | - |
dc.date.created | 2012-02-06 | - |
dc.date.created | 2012-02-06 | - |
dc.date.issued | 2007-09 | - |
dc.identifier.citation | JOURNAL OF ORGANIC CHEMISTRY, v.72, no.19, pp.7390 - 7393 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10203/90747 | - |
dc.description.abstract | [GRAPHICS] 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. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.subject | BAEYER-VILLIGER REACTIONS | - |
dc.subject | ENANTIOSELECTIVE SYNTHESIS | - |
dc.subject | ASYMMETRIC HYDROGENATION | - |
dc.subject | SECONDARY STRUCTURES | - |
dc.subject | CONJUGATE ADDITION | - |
dc.subject | LIGNAN LACTONES | - |
dc.subject | NMR-SOLUTION | - |
dc.subject | AMINO-ACIDS | - |
dc.subject | PEPTIDES | - |
dc.subject | ANALOGS | - |
dc.title | Enantiomerically pure synthesis of beta-substituted gamma-butyrolactones: A key intermediate to concise synthesis of pregabalin | - |
dc.type | Article | - |
dc.identifier.wosid | 000249371200041 | - |
dc.identifier.scopusid | 2-s2.0-34548792285 | - |
dc.type.rims | ART | - |
dc.citation.volume | 72 | - |
dc.citation.issue | 19 | - |
dc.citation.beginningpage | 7390 | - |
dc.citation.endingpage | 7393 | - |
dc.citation.publicationname | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.identifier.doi | 10.1021/jo0709605 | - |
dc.contributor.localauthor | Lee, Hee-Seung | - |
dc.contributor.nonIdAuthor | Ok, T | - |
dc.contributor.nonIdAuthor | Jeon, A | - |
dc.contributor.nonIdAuthor | Lee, J | - |
dc.contributor.nonIdAuthor | Lim, JH | - |
dc.contributor.nonIdAuthor | Hong, CS | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | BAEYER-VILLIGER REACTIONS | - |
dc.subject.keywordPlus | ENANTIOSELECTIVE SYNTHESIS | - |
dc.subject.keywordPlus | ASYMMETRIC HYDROGENATION | - |
dc.subject.keywordPlus | SECONDARY STRUCTURES | - |
dc.subject.keywordPlus | CONJUGATE ADDITION | - |
dc.subject.keywordPlus | LIGNAN LACTONES | - |
dc.subject.keywordPlus | NMR-SOLUTION | - |
dc.subject.keywordPlus | AMINO-ACIDS | - |
dc.subject.keywordPlus | PEPTIDES | - |
dc.subject.keywordPlus | ANALOGS | - |
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