Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin

Autores
Henrion, S.; Macé, A.; Vallejos, Margarita; Roisnel, T.; Carboni, B.; Villalgordo, J.M.; Carreaux, Francois
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
An efficient asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones from aldehydes and enantioenriched γ-carbamate alkenylboronates is reported. The cornerstone of this strategy is the implementation of sequential [3,3]-allyl cyanate rearrangement/allylboration/nucleophilic addition/cyclisation reactions. Diverse γ-butyrolactones such as the flavouring compounds, (+)-trans-whiskey lactone and (+)-trans-cognac lactone, as well as an advanced intermediate towards the first synthesis of natural products, (-)-nicotlactone B and (-)-galbacin, have thus been obtained.
Fil: Henrion, S.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; Francia
Fil: Macé, A.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; Francia
Fil: Vallejos, Margarita. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Química Básica y Aplicada del Nordeste Argentino. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina
Fil: Roisnel, T.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; Francia
Fil: Carboni, B.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia
Fil: Villalgordo, J.M.. Parque Tecnológico de Fuente Alamo. VillaPharma Research; España
Fil: Carreaux, Francois. Centre National de la Recherche Scientifique; Francia. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia
Materia
ASYMMETRIC SYNTHESIS
ORGANOBORON COMPOUND
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/96348
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacinHenrion, S.Macé, A.Vallejos, MargaritaRoisnel, T.Carboni, B.Villalgordo, J.M.Carreaux, FrancoisASYMMETRIC SYNTHESISORGANOBORON COMPOUNDhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1An efficient asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones from aldehydes and enantioenriched γ-carbamate alkenylboronates is reported. The cornerstone of this strategy is the implementation of sequential [3,3]-allyl cyanate rearrangement/allylboration/nucleophilic addition/cyclisation reactions. Diverse γ-butyrolactones such as the flavouring compounds, (+)-trans-whiskey lactone and (+)-trans-cognac lactone, as well as an advanced intermediate towards the first synthesis of natural products, (-)-nicotlactone B and (-)-galbacin, have thus been obtained.Fil: Henrion, S.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; FranciaFil: Macé, A.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; FranciaFil: Vallejos, Margarita. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Química Básica y Aplicada del Nordeste Argentino. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Química Básica y Aplicada del Nordeste Argentino; ArgentinaFil: Roisnel, T.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; FranciaFil: Carboni, B.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; FranciaFil: Villalgordo, J.M.. Parque Tecnológico de Fuente Alamo. VillaPharma Research; EspañaFil: Carreaux, Francois. Centre National de la Recherche Scientifique; Francia. Université de Rennes I. Institut des Sciences Chimiques de Rennes; FranciaRoyal Society of Chemistry2018-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/96348Henrion, S.; Macé, A.; Vallejos, Margarita; Roisnel, T.; Carboni, B.; et al.; Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 16; 10; 2-2018; 1672-16781477-0520CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://xlink.rsc.org/?DOI=C8OB00101Dinfo:eu-repo/semantics/altIdentifier/doi/10.1039/C8OB00101Dinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:48:18Zoai:ri.conicet.gov.ar:11336/96348instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-11-12 09:48:18.856CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin
title Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin
spellingShingle Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin
Henrion, S.
ASYMMETRIC SYNTHESIS
ORGANOBORON COMPOUND
title_short Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin
title_full Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin
title_fullStr Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin
title_full_unstemmed Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin
title_sort Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin
dc.creator.none.fl_str_mv Henrion, S.
Macé, A.
Vallejos, Margarita
Roisnel, T.
Carboni, B.
Villalgordo, J.M.
Carreaux, Francois
author Henrion, S.
author_facet Henrion, S.
Macé, A.
Vallejos, Margarita
Roisnel, T.
Carboni, B.
Villalgordo, J.M.
Carreaux, Francois
author_role author
author2 Macé, A.
Vallejos, Margarita
Roisnel, T.
Carboni, B.
Villalgordo, J.M.
Carreaux, Francois
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv ASYMMETRIC SYNTHESIS
ORGANOBORON COMPOUND
topic ASYMMETRIC SYNTHESIS
ORGANOBORON COMPOUND
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv An efficient asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones from aldehydes and enantioenriched γ-carbamate alkenylboronates is reported. The cornerstone of this strategy is the implementation of sequential [3,3]-allyl cyanate rearrangement/allylboration/nucleophilic addition/cyclisation reactions. Diverse γ-butyrolactones such as the flavouring compounds, (+)-trans-whiskey lactone and (+)-trans-cognac lactone, as well as an advanced intermediate towards the first synthesis of natural products, (-)-nicotlactone B and (-)-galbacin, have thus been obtained.
Fil: Henrion, S.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; Francia
Fil: Macé, A.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; Francia
Fil: Vallejos, Margarita. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Química Básica y Aplicada del Nordeste Argentino. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina
Fil: Roisnel, T.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; Francia
Fil: Carboni, B.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia
Fil: Villalgordo, J.M.. Parque Tecnológico de Fuente Alamo. VillaPharma Research; España
Fil: Carreaux, Francois. Centre National de la Recherche Scientifique; Francia. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia
description An efficient asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones from aldehydes and enantioenriched γ-carbamate alkenylboronates is reported. The cornerstone of this strategy is the implementation of sequential [3,3]-allyl cyanate rearrangement/allylboration/nucleophilic addition/cyclisation reactions. Diverse γ-butyrolactones such as the flavouring compounds, (+)-trans-whiskey lactone and (+)-trans-cognac lactone, as well as an advanced intermediate towards the first synthesis of natural products, (-)-nicotlactone B and (-)-galbacin, have thus been obtained.
publishDate 2018
dc.date.none.fl_str_mv 2018-02
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/96348
Henrion, S.; Macé, A.; Vallejos, Margarita; Roisnel, T.; Carboni, B.; et al.; Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 16; 10; 2-2018; 1672-1678
1477-0520
CONICET Digital
CONICET
url http://hdl.handle.net/11336/96348
identifier_str_mv Henrion, S.; Macé, A.; Vallejos, Margarita; Roisnel, T.; Carboni, B.; et al.; Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 16; 10; 2-2018; 1672-1678
1477-0520
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://xlink.rsc.org/?DOI=C8OB00101D
info:eu-repo/semantics/altIdentifier/doi/10.1039/C8OB00101D
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1848598000426811392
score 13.24909

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