Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester

The retro-Dieckmann reaction has been used as a stereodivergent synthetic tool on N-Boc-7-azabicyclo[2.2.1]heptan-2-one-1-carboxylic acid methyl ester to obtain enantiopure trans- and cis-5-(carboxymethyl)pyrrolidine-2-carboxylic acid methyl esters. These disubstituted pyrrolidines have been used as...

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Autores: Avenoza, A. [0000-0002-5465-3555], Barriobero, J.I. [0000-0003-3822-0634], Busto, J.H. [0000-0003-4403-4790], Peregrina, J.M. [0000-0003-3778-7065]
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2003
País:España
Institución:Universidad de La Rioja (UR)
Repositorio:RIUR. Repositorio Institucional de la Universidad de La Rioja
OAI Identifier:oai:portal.dialnet.es:doc/5bbc690ab750603269e81403
Acceso en línea:https://investigacion.unirioja.es/documentos/5bbc690ab750603269e81403
Access Level:acceso abierto
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spelling Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl EsterAvenoza, A. [0000-0002-5465-3555]Barriobero, J.I. [0000-0003-3822-0634]Busto, J.H. [0000-0003-4403-4790]Peregrina, J.M. [0000-0003-3778-7065]The retro-Dieckmann reaction has been used as a stereodivergent synthetic tool on N-Boc-7-azabicyclo[2.2.1]heptan-2-one-1-carboxylic acid methyl ester to obtain enantiopure trans- and cis-5-(carboxymethyl)pyrrolidine-2-carboxylic acid methyl esters. These disubstituted pyrrolidines have been used as starting materials to develop concise and straightforward syntheses of all four stereoisomers of carbapenam-3-carboxylic acid methyl esters. In this way, we have confirmed unequivocally the stereochemistry of two carbapenams isolated from strains of Serratia and Erwinia species.2003info:eu-repo/semantics/articleSubtype: Articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://investigacion.unirioja.es/documentos/5bbc690ab750603269e81403reponame:RIUR. Repositorio Institucional de la Universidad de La Riojainstname:Universidad de La Rioja (UR)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1021/JO026804+info:eu-repo/semantics/altIdentifier/wos/WOS:000181953700046info:eu-repo/semantics/altIdentifier/pmid/12662066info:eu-repo/semantics/altIdentifier/pissn/0022-3263Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester, 2003, vol. 68, núm. 7, pág. 2889-2894info:eu-repo/semantics/openAccessoai:portal.dialnet.es:doc/5bbc690ab750603269e814032026-06-14T12:47:17Z
dc.title.none.fl_str_mv Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester
title Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester
spellingShingle Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester
Avenoza, A. [0000-0002-5465-3555]
title_short Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester
title_full Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester
title_fullStr Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester
title_full_unstemmed Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester
title_sort Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester
dc.creator.none.fl_str_mv Avenoza, A. [0000-0002-5465-3555]
Barriobero, J.I. [0000-0003-3822-0634]
Busto, J.H. [0000-0003-4403-4790]
Peregrina, J.M. [0000-0003-3778-7065]
author Avenoza, A. [0000-0002-5465-3555]
author_facet Avenoza, A. [0000-0002-5465-3555]
Barriobero, J.I. [0000-0003-3822-0634]
Busto, J.H. [0000-0003-4403-4790]
Peregrina, J.M. [0000-0003-3778-7065]
author_role author
author2 Barriobero, J.I. [0000-0003-3822-0634]
Busto, J.H. [0000-0003-4403-4790]
Peregrina, J.M. [0000-0003-3778-7065]
author2_role author
author
author
description The retro-Dieckmann reaction has been used as a stereodivergent synthetic tool on N-Boc-7-azabicyclo[2.2.1]heptan-2-one-1-carboxylic acid methyl ester to obtain enantiopure trans- and cis-5-(carboxymethyl)pyrrolidine-2-carboxylic acid methyl esters. These disubstituted pyrrolidines have been used as starting materials to develop concise and straightforward syntheses of all four stereoisomers of carbapenam-3-carboxylic acid methyl esters. In this way, we have confirmed unequivocally the stereochemistry of two carbapenams isolated from strains of Serratia and Erwinia species.
publishDate 2003
dc.date.none.fl_str_mv 2003
dc.type.none.fl_str_mv info:eu-repo/semantics/article
Subtype: Article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://investigacion.unirioja.es/documentos/5bbc690ab750603269e81403
url https://investigacion.unirioja.es/documentos/5bbc690ab750603269e81403
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/JO026804+
info:eu-repo/semantics/altIdentifier/wos/WOS:000181953700046
info:eu-repo/semantics/altIdentifier/pmid/12662066
info:eu-repo/semantics/altIdentifier/pissn/0022-3263
Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester, 2003, vol. 68, núm. 7, pág. 2889-2894
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:RIUR. Repositorio Institucional de la Universidad de La Rioja
instname:Universidad de La Rioja (UR)
instname_str Universidad de La Rioja (UR)
reponame_str RIUR. Repositorio Institucional de la Universidad de La Rioja
collection RIUR. Repositorio Institucional de la Universidad de La Rioja
repository.name.fl_str_mv
repository.mail.fl_str_mv
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