Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins

Autores
Maes, Dominick; Riveiro, Maria Eugenia; Shayo, Carina Claudia; Davio, Carlos Alberto; Debenedetti, Silvia Laura; De Kimpe, Norbert
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis of five naturally occurring polyoxygenated coumarins is described. It concerns two 5,6,7-trioxygenated coumarins, i.e., 6-hydroxy-5,7-dimethoxycoumarin (fraxinol) 1 and 5,6,7-trimethoxycoumarin 2, and three 5,7,8-trioxygenated coumarins, i.e., 8-hydroxy-5,7-dimethoxycoumarin (leptodactylone) 3, 5,7,8-trimethoxycoumarin 4 and 8-(3-methyl-2-butenyloxy)-5,7-dimethoxycoumarin (artanin) 5. Key feature of the synthetic pathway is the synthesis of suitable tetraoxygenated benzaldehydes, which are then converted to the corresponding coumarins via a Wittig reaction.
Fil: Maes, Dominick. University of Ghent; Bélgica
Fil: Riveiro, Maria Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Shayo, Carina Claudia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; Argentina
Fil: Davio, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Debenedetti, Silvia Laura. Universidad Nacional de La Plata. Facultad de Ciencias Exactas; Argentina
Fil: De Kimpe, Norbert. University of Ghent; Bélgica
Materia
Coumarins
Total Synthesis
Wittig Reaction
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/25751
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarinsMaes, DominickRiveiro, Maria EugeniaShayo, Carina ClaudiaDavio, Carlos AlbertoDebenedetti, Silvia LauraDe Kimpe, NorbertCoumarinsTotal SynthesisWittig ReactionThe synthesis of five naturally occurring polyoxygenated coumarins is described. It concerns two 5,6,7-trioxygenated coumarins, i.e., 6-hydroxy-5,7-dimethoxycoumarin (fraxinol) 1 and 5,6,7-trimethoxycoumarin 2, and three 5,7,8-trioxygenated coumarins, i.e., 8-hydroxy-5,7-dimethoxycoumarin (leptodactylone) 3, 5,7,8-trimethoxycoumarin 4 and 8-(3-methyl-2-butenyloxy)-5,7-dimethoxycoumarin (artanin) 5. Key feature of the synthetic pathway is the synthesis of suitable tetraoxygenated benzaldehydes, which are then converted to the corresponding coumarins via a Wittig reaction.Fil: Maes, Dominick. University of Ghent; BélgicaFil: Riveiro, Maria Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; ArgentinaFil: Shayo, Carina Claudia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; ArgentinaFil: Davio, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; ArgentinaFil: Debenedetti, Silvia Laura. Universidad Nacional de La Plata. Facultad de Ciencias Exactas; ArgentinaFil: De Kimpe, Norbert. University of Ghent; BélgicaElsevier2008info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/25751Maes, Dominick; Riveiro, Maria Eugenia; Shayo, Carina Claudia; Davio, Carlos Alberto; Debenedetti, Silvia Laura; et al.; Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins; Elsevier; Tetrahedron; 64; 19; -1-2008; 4438-44430040-40200040-4020CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040402008003074info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2008.02.059info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:56:49Zoai:ri.conicet.gov.ar:11336/25751instacron: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:34982025-10-15 14:56:49.747CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
title Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
spellingShingle Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
Maes, Dominick
Coumarins
Total Synthesis
Wittig Reaction
title_short Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
title_full Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
title_fullStr Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
title_full_unstemmed Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
title_sort Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
dc.creator.none.fl_str_mv Maes, Dominick
Riveiro, Maria Eugenia
Shayo, Carina Claudia
Davio, Carlos Alberto
Debenedetti, Silvia Laura
De Kimpe, Norbert
author Maes, Dominick
author_facet Maes, Dominick
Riveiro, Maria Eugenia
Shayo, Carina Claudia
Davio, Carlos Alberto
Debenedetti, Silvia Laura
De Kimpe, Norbert
author_role author
author2 Riveiro, Maria Eugenia
Shayo, Carina Claudia
Davio, Carlos Alberto
Debenedetti, Silvia Laura
De Kimpe, Norbert
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Coumarins
Total Synthesis
Wittig Reaction
topic Coumarins
Total Synthesis
Wittig Reaction
dc.description.none.fl_txt_mv The synthesis of five naturally occurring polyoxygenated coumarins is described. It concerns two 5,6,7-trioxygenated coumarins, i.e., 6-hydroxy-5,7-dimethoxycoumarin (fraxinol) 1 and 5,6,7-trimethoxycoumarin 2, and three 5,7,8-trioxygenated coumarins, i.e., 8-hydroxy-5,7-dimethoxycoumarin (leptodactylone) 3, 5,7,8-trimethoxycoumarin 4 and 8-(3-methyl-2-butenyloxy)-5,7-dimethoxycoumarin (artanin) 5. Key feature of the synthetic pathway is the synthesis of suitable tetraoxygenated benzaldehydes, which are then converted to the corresponding coumarins via a Wittig reaction.
Fil: Maes, Dominick. University of Ghent; Bélgica
Fil: Riveiro, Maria Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Shayo, Carina Claudia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; Argentina
Fil: Davio, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Debenedetti, Silvia Laura. Universidad Nacional de La Plata. Facultad de Ciencias Exactas; Argentina
Fil: De Kimpe, Norbert. University of Ghent; Bélgica
description The synthesis of five naturally occurring polyoxygenated coumarins is described. It concerns two 5,6,7-trioxygenated coumarins, i.e., 6-hydroxy-5,7-dimethoxycoumarin (fraxinol) 1 and 5,6,7-trimethoxycoumarin 2, and three 5,7,8-trioxygenated coumarins, i.e., 8-hydroxy-5,7-dimethoxycoumarin (leptodactylone) 3, 5,7,8-trimethoxycoumarin 4 and 8-(3-methyl-2-butenyloxy)-5,7-dimethoxycoumarin (artanin) 5. Key feature of the synthetic pathway is the synthesis of suitable tetraoxygenated benzaldehydes, which are then converted to the corresponding coumarins via a Wittig reaction.
publishDate 2008
dc.date.none.fl_str_mv 2008
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/11336/25751
Maes, Dominick; Riveiro, Maria Eugenia; Shayo, Carina Claudia; Davio, Carlos Alberto; Debenedetti, Silvia Laura; et al.; Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins; Elsevier; Tetrahedron; 64; 19; -1-2008; 4438-4443
0040-4020
0040-4020
CONICET Digital
CONICET
url http://hdl.handle.net/11336/25751
identifier_str_mv Maes, Dominick; Riveiro, Maria Eugenia; Shayo, Carina Claudia; Davio, Carlos Alberto; Debenedetti, Silvia Laura; et al.; Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins; Elsevier; Tetrahedron; 64; 19; -1-2008; 4438-4443
0040-4020
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://www.sciencedirect.com/science/article/pii/S0040402008003074
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2008.02.059
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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
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score 13.22299

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