Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool

Autores
Jäger, Sebastian Nicolas; Porta, Exequiel Oscar Jesús; Labadie, Guillermo Roberto
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A diversity-oriented approach for the synthesis of various structurally different prenylated alcohols from readily accessible and common precursors was developed. With varying approaches, this article describes some successful examples of a Friedel–Crafts alkylation using methoxyphenols and different prenyl alcohols (geraniol and (E,E)-farnesol). We demonstrated that just by varying the stoichiometry of the Lewis acid used, the course of the reaction can be shifted to produce the alkylated or the cyclized product. Eighteen unique products were obtained with good isolated yields by direct alkylation with or without a consecutive (Formula presented.) -cationic cyclization.
Fil: Jäger, Sebastian Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Porta, Exequiel Oscar Jesús. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Labadie, Guillermo Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
FRIEDEL–CRAFTS ALKYLATION
PHENOLS
PRENYLATED NATURAL PRODUCTS
SELECTIVE C-PRENYLATION
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:11336/52429
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity toolJäger, Sebastian NicolasPorta, Exequiel Oscar JesúsLabadie, Guillermo RobertoFRIEDEL–CRAFTS ALKYLATIONPHENOLSPRENYLATED NATURAL PRODUCTSSELECTIVE C-PRENYLATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A diversity-oriented approach for the synthesis of various structurally different prenylated alcohols from readily accessible and common precursors was developed. With varying approaches, this article describes some successful examples of a Friedel–Crafts alkylation using methoxyphenols and different prenyl alcohols (geraniol and (E,E)-farnesol). We demonstrated that just by varying the stoichiometry of the Lewis acid used, the course of the reaction can be shifted to produce the alkylated or the cyclized product. Eighteen unique products were obtained with good isolated yields by direct alkylation with or without a consecutive (Formula presented.) -cationic cyclization.Fil: Jäger, Sebastian Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Porta, Exequiel Oscar Jesús. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Labadie, Guillermo Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaSpringer2016-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/52429Jäger, Sebastian Nicolas; Porta, Exequiel Oscar Jesús; Labadie, Guillermo Roberto; Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool; Springer; Molecular Diversity; 20; 2; 5-2016; 407-4191381-1991CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1007/s11030-015-9644-9info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs11030-015-9644-9info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:44:13Zoai:ri.conicet.gov.ar:11336/52429instacron: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 14:44:13.469CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool
title Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool
spellingShingle Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool
Jäger, Sebastian Nicolas
FRIEDEL–CRAFTS ALKYLATION
PHENOLS
PRENYLATED NATURAL PRODUCTS
SELECTIVE C-PRENYLATION
title_short Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool
title_full Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool
title_fullStr Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool
title_full_unstemmed Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool
title_sort Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool
dc.creator.none.fl_str_mv Jäger, Sebastian Nicolas
Porta, Exequiel Oscar Jesús
Labadie, Guillermo Roberto
author Jäger, Sebastian Nicolas
author_facet Jäger, Sebastian Nicolas
Porta, Exequiel Oscar Jesús
Labadie, Guillermo Roberto
author_role author
author2 Porta, Exequiel Oscar Jesús
Labadie, Guillermo Roberto
author2_role author
author
dc.subject.none.fl_str_mv FRIEDEL–CRAFTS ALKYLATION
PHENOLS
PRENYLATED NATURAL PRODUCTS
SELECTIVE C-PRENYLATION
topic FRIEDEL–CRAFTS ALKYLATION
PHENOLS
PRENYLATED NATURAL PRODUCTS
SELECTIVE C-PRENYLATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A diversity-oriented approach for the synthesis of various structurally different prenylated alcohols from readily accessible and common precursors was developed. With varying approaches, this article describes some successful examples of a Friedel–Crafts alkylation using methoxyphenols and different prenyl alcohols (geraniol and (E,E)-farnesol). We demonstrated that just by varying the stoichiometry of the Lewis acid used, the course of the reaction can be shifted to produce the alkylated or the cyclized product. Eighteen unique products were obtained with good isolated yields by direct alkylation with or without a consecutive (Formula presented.) -cationic cyclization.
Fil: Jäger, Sebastian Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Porta, Exequiel Oscar Jesús. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Labadie, Guillermo Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description A diversity-oriented approach for the synthesis of various structurally different prenylated alcohols from readily accessible and common precursors was developed. With varying approaches, this article describes some successful examples of a Friedel–Crafts alkylation using methoxyphenols and different prenyl alcohols (geraniol and (E,E)-farnesol). We demonstrated that just by varying the stoichiometry of the Lewis acid used, the course of the reaction can be shifted to produce the alkylated or the cyclized product. Eighteen unique products were obtained with good isolated yields by direct alkylation with or without a consecutive (Formula presented.) -cationic cyclization.
publishDate 2016
dc.date.none.fl_str_mv 2016-05
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/11336/52429
Jäger, Sebastian Nicolas; Porta, Exequiel Oscar Jesús; Labadie, Guillermo Roberto; Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool; Springer; Molecular Diversity; 20; 2; 5-2016; 407-419
1381-1991
CONICET Digital
CONICET
url http://hdl.handle.net/11336/52429
identifier_str_mv Jäger, Sebastian Nicolas; Porta, Exequiel Oscar Jesús; Labadie, Guillermo Roberto; Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool; Springer; Molecular Diversity; 20; 2; 5-2016; 407-419
1381-1991
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1007/s11030-015-9644-9
info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs11030-015-9644-9
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
application/pdf
dc.publisher.none.fl_str_mv Springer
publisher.none.fl_str_mv Springer
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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