Stereocontrolled access to enantiopure to enantiopure 7-substituted cis- and trans-octahydroindoles

Cyclocondensation of (R)-phenylglycinol with stereoisomeric mixtures (racemates, cis/trans) of 3-substituted 2- oxocyclohexaneacetates stereoselectively afforded tricyclic oxazoloindolone lactams, from which straightforward procedures for the stereocontrolled formation of enantiopure 7-substituted o...

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Autores: Ghirardi, Elena, Griera Farres, Rosa, Piccichè, Miriam, Molins i Grau, Elies, Fernández Cadenas, Israel, Bosch Cartes, Joan, Amat Tusón, Mercedes
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/108046
Acceso en línea:https://hdl.handle.net/2445/108046
Access Level:acceso abierto
Palabra clave:Lactames
Síntesi asimètrica
Lactams
Asymmetric synthesis
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spelling Stereocontrolled access to enantiopure to enantiopure 7-substituted cis- and trans-octahydroindolesGhirardi, ElenaGriera Farres, RosaPiccichè, MiriamMolins i Grau, EliesFernández Cadenas, IsraelBosch Cartes, JoanAmat Tusón, MercedesLactamesSíntesi asimètricaLactamsAsymmetric synthesisCyclocondensation of (R)-phenylglycinol with stereoisomeric mixtures (racemates, cis/trans) of 3-substituted 2- oxocyclohexaneacetates stereoselectively afforded tricyclic oxazoloindolone lactams, from which straightforward procedures for the stereocontrolled formation of enantiopure 7-substituted octahydroindoles with a variety of stereochemical patterns have been developed. The methodology has been successfully applied to the synthesis of (+)-α-lycorane.American Chemical Society2016info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/108046Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: https://doi.org/10.1021/acs.orglett.6b02861Organic Letters, 2016, vol. 18, num. 22, p. 5836-5839https://doi.org/10.1021/acs.orglett.6b02861(c) American Chemical Society , 2016info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1080462026-05-27T06:46:51Z
dc.title.none.fl_str_mv Stereocontrolled access to enantiopure to enantiopure 7-substituted cis- and trans-octahydroindoles
title Stereocontrolled access to enantiopure to enantiopure 7-substituted cis- and trans-octahydroindoles
spellingShingle Stereocontrolled access to enantiopure to enantiopure 7-substituted cis- and trans-octahydroindoles
Ghirardi, Elena
Lactames
Síntesi asimètrica
Lactams
Asymmetric synthesis
title_short Stereocontrolled access to enantiopure to enantiopure 7-substituted cis- and trans-octahydroindoles
title_full Stereocontrolled access to enantiopure to enantiopure 7-substituted cis- and trans-octahydroindoles
title_fullStr Stereocontrolled access to enantiopure to enantiopure 7-substituted cis- and trans-octahydroindoles
title_full_unstemmed Stereocontrolled access to enantiopure to enantiopure 7-substituted cis- and trans-octahydroindoles
title_sort Stereocontrolled access to enantiopure to enantiopure 7-substituted cis- and trans-octahydroindoles
dc.creator.none.fl_str_mv Ghirardi, Elena
Griera Farres, Rosa
Piccichè, Miriam
Molins i Grau, Elies
Fernández Cadenas, Israel
Bosch Cartes, Joan
Amat Tusón, Mercedes
author Ghirardi, Elena
author_facet Ghirardi, Elena
Griera Farres, Rosa
Piccichè, Miriam
Molins i Grau, Elies
Fernández Cadenas, Israel
Bosch Cartes, Joan
Amat Tusón, Mercedes
author_role author
author2 Griera Farres, Rosa
Piccichè, Miriam
Molins i Grau, Elies
Fernández Cadenas, Israel
Bosch Cartes, Joan
Amat Tusón, Mercedes
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Lactames
Síntesi asimètrica
Lactams
Asymmetric synthesis
topic Lactames
Síntesi asimètrica
Lactams
Asymmetric synthesis
description Cyclocondensation of (R)-phenylglycinol with stereoisomeric mixtures (racemates, cis/trans) of 3-substituted 2- oxocyclohexaneacetates stereoselectively afforded tricyclic oxazoloindolone lactams, from which straightforward procedures for the stereocontrolled formation of enantiopure 7-substituted octahydroindoles with a variety of stereochemical patterns have been developed. The methodology has been successfully applied to the synthesis of (+)-α-lycorane.
publishDate 2016
dc.date.none.fl_str_mv 2016
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/108046
url https://hdl.handle.net/2445/108046
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1021/acs.orglett.6b02861
Organic Letters, 2016, vol. 18, num. 22, p. 5836-5839
https://doi.org/10.1021/acs.orglett.6b02861
dc.rights.none.fl_str_mv (c) American Chemical Society , 2016
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) American Chemical Society , 2016
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.300719

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