Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C

A synthesis of (+)-gephyrotoxin 287C using, (S)-phenylglycinol-derived tricyclic lactam 7 as the starting enantiomeric scaffold is reported. From the stereochemical standpoint, the key steps are the generation of the DHQ C-5 stereocenter by hydrogenation of the C-C double bond, removal of the chiral...

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Detalles Bibliográficos
Autores: Piccichè, Miriam, Pinto, Alexandre, Griera Farres, Rosa, Bosch Cartes, Joan, Amat Tusón, Mercedes
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/127597
Acceso en línea:https://hdl.handle.net/2445/127597
Access Level:acceso abierto
Palabra clave:Síntesi asimètrica
Lactames
Catàlisi asimètrica
Asymmetric synthesis
Lactams
Enantioselective catalysis
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spelling Enantioselective Total Synthesis of (+)-Gephyrotoxin 287CPiccichè, MiriamPinto, AlexandreGriera Farres, RosaBosch Cartes, JoanAmat Tusón, MercedesSíntesi asimètricaLactamesCatàlisi asimètricaAsymmetric synthesisLactamsEnantioselective catalysisA synthesis of (+)-gephyrotoxin 287C using, (S)-phenylglycinol-derived tricyclic lactam 7 as the starting enantiomeric scaffold is reported. From the stereochemical standpoint, the key steps are the generation of the DHQ C-5 stereocenter by hydrogenation of the C-C double bond, removal of the chiral inductor to give a cis-DHQ introduction of the DHQ C-2 substituent, completion of the (Z)-enyne moiety, and generation of the C-1 stereocenter during closure of the pyrrolidine ring.American Chemical Society2017info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/127597Articles 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.7b03381Organic Letters, 2017, vol. 19, num. 24, p. 6654-6657https://doi.org/10.1021/acs.orglett.7b03381(c) American Chemical Society , 2017info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1275972026-05-27T06:46:51Z
dc.title.none.fl_str_mv Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C
title Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C
spellingShingle Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C
Piccichè, Miriam
Síntesi asimètrica
Lactames
Catàlisi asimètrica
Asymmetric synthesis
Lactams
Enantioselective catalysis
title_short Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C
title_full Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C
title_fullStr Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C
title_full_unstemmed Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C
title_sort Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C
dc.creator.none.fl_str_mv Piccichè, Miriam
Pinto, Alexandre
Griera Farres, Rosa
Bosch Cartes, Joan
Amat Tusón, Mercedes
author Piccichè, Miriam
author_facet Piccichè, Miriam
Pinto, Alexandre
Griera Farres, Rosa
Bosch Cartes, Joan
Amat Tusón, Mercedes
author_role author
author2 Pinto, Alexandre
Griera Farres, Rosa
Bosch Cartes, Joan
Amat Tusón, Mercedes
author2_role author
author
author
author
dc.subject.none.fl_str_mv Síntesi asimètrica
Lactames
Catàlisi asimètrica
Asymmetric synthesis
Lactams
Enantioselective catalysis
topic Síntesi asimètrica
Lactames
Catàlisi asimètrica
Asymmetric synthesis
Lactams
Enantioselective catalysis
description A synthesis of (+)-gephyrotoxin 287C using, (S)-phenylglycinol-derived tricyclic lactam 7 as the starting enantiomeric scaffold is reported. From the stereochemical standpoint, the key steps are the generation of the DHQ C-5 stereocenter by hydrogenation of the C-C double bond, removal of the chiral inductor to give a cis-DHQ introduction of the DHQ C-2 substituent, completion of the (Z)-enyne moiety, and generation of the C-1 stereocenter during closure of the pyrrolidine ring.
publishDate 2017
dc.date.none.fl_str_mv 2017
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/2445/127597
url https://hdl.handle.net/2445/127597
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.7b03381
Organic Letters, 2017, vol. 19, num. 24, p. 6654-6657
https://doi.org/10.1021/acs.orglett.7b03381
dc.rights.none.fl_str_mv (c) American Chemical Society , 2017
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) American Chemical Society , 2017
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
_version_ 1869414788647354368
score 15,300724

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