An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit

Autores
Gogoi, Pranjal; Sigüeiro, Rita; Eduardo, Silvina Laura; Mouriño, Antonio
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Chemical equation presented Daily vitamins: A mild, general, and highly stereoselective Pd0-catalyzed cascade to the triene system of the hoi mone 1α,25-dihydroxyvitamin D3 and six representative analogues is reported. The intramolecular cyclization of an enol-triflate (lower fragment) followed in situ by Suzuki Miyaura coupling with an alkenyl boronic ester (upper fragment, also efficiently prepared by Pd0-catalyzed coupling) in equimolar amounts under protic conditions is ideal for the preparation of small amounts of new vitamin D analogues for biological testing (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
Fil: Gogoi, Pranjal. Universidad de Santiago de Compostela; España. Consejo Superior de Investigaciones Científicas; España
Fil: Sigüeiro, Rita. Consejo Superior de Investigaciones Científicas; España. Universidad de Santiago de Compostela; España
Fil: Eduardo, Silvina Laura. Consejo Superior de Investigaciones Científicas; España. Universidad de Santiago de Compostela; España. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Mouriño, Antonio. Consejo Superior de Investigaciones Científicas; España. Universidad de Santiago de Compostela; España
Materia
Homogeneous Catalysis
Natural Products Palladium
Synthesis Design
Vitamins
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/70592
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/70592
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unitGogoi, PranjalSigüeiro, RitaEduardo, Silvina LauraMouriño, AntonioHomogeneous CatalysisNatural Products PalladiumSynthesis DesignVitaminshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Chemical equation presented Daily vitamins: A mild, general, and highly stereoselective Pd0-catalyzed cascade to the triene system of the hoi mone 1α,25-dihydroxyvitamin D3 and six representative analogues is reported. The intramolecular cyclization of an enol-triflate (lower fragment) followed in situ by Suzuki Miyaura coupling with an alkenyl boronic ester (upper fragment, also efficiently prepared by Pd0-catalyzed coupling) in equimolar amounts under protic conditions is ideal for the preparation of small amounts of new vitamin D analogues for biological testing (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.Fil: Gogoi, Pranjal. Universidad de Santiago de Compostela; España. Consejo Superior de Investigaciones Científicas; EspañaFil: Sigüeiro, Rita. Consejo Superior de Investigaciones Científicas; España. Universidad de Santiago de Compostela; EspañaFil: Eduardo, Silvina Laura. Consejo Superior de Investigaciones Científicas; España. Universidad de Santiago de Compostela; España. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Mouriño, Antonio. Consejo Superior de Investigaciones Científicas; España. Universidad de Santiago de Compostela; EspañaWiley VCH Verlag2010-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/70592Gogoi, Pranjal; Sigüeiro, Rita; Eduardo, Silvina Laura; Mouriño, Antonio; An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit; Wiley VCH Verlag; Chemistry- A European Journal; 16; 5; 2-2010; 1432-14350947-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/chem.200902972info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.200902972info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-12-03T08:33:02Zoai:ri.conicet.gov.ar:11336/70592instacron: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:34982025-12-03 08:33:02.632CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit
title An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit
spellingShingle An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit
Gogoi, Pranjal
Homogeneous Catalysis
Natural Products Palladium
Synthesis Design
Vitamins
title_short An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit
title_full An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit
title_fullStr An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit
title_full_unstemmed An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit
title_sort An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit
dc.creator.none.fl_str_mv Gogoi, Pranjal
Sigüeiro, Rita
Eduardo, Silvina Laura
Mouriño, Antonio
author Gogoi, Pranjal
author_facet Gogoi, Pranjal
Sigüeiro, Rita
Eduardo, Silvina Laura
Mouriño, Antonio
author_role author
author2 Sigüeiro, Rita
Eduardo, Silvina Laura
Mouriño, Antonio
author2_role author
author
author
dc.subject.none.fl_str_mv Homogeneous Catalysis
Natural Products Palladium
Synthesis Design
Vitamins
topic Homogeneous Catalysis
Natural Products Palladium
Synthesis Design
Vitamins
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Chemical equation presented Daily vitamins: A mild, general, and highly stereoselective Pd0-catalyzed cascade to the triene system of the hoi mone 1α,25-dihydroxyvitamin D3 and six representative analogues is reported. The intramolecular cyclization of an enol-triflate (lower fragment) followed in situ by Suzuki Miyaura coupling with an alkenyl boronic ester (upper fragment, also efficiently prepared by Pd0-catalyzed coupling) in equimolar amounts under protic conditions is ideal for the preparation of small amounts of new vitamin D analogues for biological testing (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
Fil: Gogoi, Pranjal. Universidad de Santiago de Compostela; España. Consejo Superior de Investigaciones Científicas; España
Fil: Sigüeiro, Rita. Consejo Superior de Investigaciones Científicas; España. Universidad de Santiago de Compostela; España
Fil: Eduardo, Silvina Laura. Consejo Superior de Investigaciones Científicas; España. Universidad de Santiago de Compostela; España. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Mouriño, Antonio. Consejo Superior de Investigaciones Científicas; España. Universidad de Santiago de Compostela; España
description Chemical equation presented Daily vitamins: A mild, general, and highly stereoselective Pd0-catalyzed cascade to the triene system of the hoi mone 1α,25-dihydroxyvitamin D3 and six representative analogues is reported. The intramolecular cyclization of an enol-triflate (lower fragment) followed in situ by Suzuki Miyaura coupling with an alkenyl boronic ester (upper fragment, also efficiently prepared by Pd0-catalyzed coupling) in equimolar amounts under protic conditions is ideal for the preparation of small amounts of new vitamin D analogues for biological testing (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
publishDate 2010
dc.date.none.fl_str_mv 2010-02
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/11336/70592
Gogoi, Pranjal; Sigüeiro, Rita; Eduardo, Silvina Laura; Mouriño, Antonio; An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit; Wiley VCH Verlag; Chemistry- A European Journal; 16; 5; 2-2010; 1432-1435
0947-6539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/70592
identifier_str_mv Gogoi, Pranjal; Sigüeiro, Rita; Eduardo, Silvina Laura; Mouriño, Antonio; An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit; Wiley VCH Verlag; Chemistry- A European Journal; 16; 5; 2-2010; 1432-1435
0947-6539
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.200902972
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.200902972
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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 12.764688

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