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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/96348
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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 Técnicas2025-09-29T10:08:42Zoai: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:34982025-09-29 10:08:43.252CONICET 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_ |
1844613957715755008 |
score |
13.070432 |