Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions

Autores
Pergomet, Jorgelina Leonor; Bracca, Andrea Beatriz Juana; Kaufman, Teodoro Saul
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The concise and efficient total syntheses of the naturally-occurring coumarin derivatives gerberinol I, and the pterophyllins 2 and 4, from 5-methyl-4-hydroxycoumarin as a common precursor employing different Casnati-Skattebøl reaction conditions, are reported. The synthesis of the key intermediate coumarin was achieved by the organocatalytic condensation of acetylacetone and crotonaldehyde followed by a LiCl-assisted cyclization, CuCl2-promoted aromatization and a final Et2CO3-mediated cyclization. A Casnati-Skattebøl formylation under high-temperature conditions afforded gerberinol I, whereas milder conditions resulted in an unstable 3-formyl-4-hydroxycoumarin derivative, which was subjected to a basic alumina-mediated one pot O-alkylation with chloroacetone and intramolecular aldolization to furnish pterophyllin 4. Wittig methylenation of the latter conveniently afforded pterophyllin 2.
Fil: Pergomet, Jorgelina Leonor. 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: Bracca, Andrea Beatriz Juana. 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: Kaufman, Teodoro Saul. 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
PTEROPHYLLINES 2 AND 4
GERBERINOL I
CASNATI-SKATTEBOL
NATURAL PRODUCT SYNTHESIS
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:11336/63886
Acceder
id CONICETDig_7ff250e4ccb24510161efe6eba87df4b
oai_identifier_str oai:ri.conicet.gov.ar:11336/63886
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditionsPergomet, Jorgelina LeonorBracca, Andrea Beatriz JuanaKaufman, Teodoro SaulPTEROPHYLLINES 2 AND 4GERBERINOL ICASNATI-SKATTEBOLNATURAL PRODUCT SYNTHESIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The concise and efficient total syntheses of the naturally-occurring coumarin derivatives gerberinol I, and the pterophyllins 2 and 4, from 5-methyl-4-hydroxycoumarin as a common precursor employing different Casnati-Skattebøl reaction conditions, are reported. The synthesis of the key intermediate coumarin was achieved by the organocatalytic condensation of acetylacetone and crotonaldehyde followed by a LiCl-assisted cyclization, CuCl2-promoted aromatization and a final Et2CO3-mediated cyclization. A Casnati-Skattebøl formylation under high-temperature conditions afforded gerberinol I, whereas milder conditions resulted in an unstable 3-formyl-4-hydroxycoumarin derivative, which was subjected to a basic alumina-mediated one pot O-alkylation with chloroacetone and intramolecular aldolization to furnish pterophyllin 4. Wittig methylenation of the latter conveniently afforded pterophyllin 2.Fil: Pergomet, Jorgelina Leonor. 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: Bracca, Andrea Beatriz Juana. 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: Kaufman, Teodoro Saul. 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; ArgentinaRoyal Society of Chemistry2017-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/63886Pergomet, Jorgelina Leonor; Bracca, Andrea Beatriz Juana; Kaufman, Teodoro Saul; Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 15; 33; 8-2017; 7040-70491477-0520CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB01471Finfo:eu-repo/semantics/altIdentifier/doi/10.1039/C7OB01471Finfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:14:15Zoai:ri.conicet.gov.ar:11336/63886instacron: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 10:14:15.692CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions
title Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions
spellingShingle Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions
Pergomet, Jorgelina Leonor
PTEROPHYLLINES 2 AND 4
GERBERINOL I
CASNATI-SKATTEBOL
NATURAL PRODUCT SYNTHESIS
title_short Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions
title_full Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions
title_fullStr Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions
title_full_unstemmed Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions
title_sort Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions
dc.creator.none.fl_str_mv Pergomet, Jorgelina Leonor
Bracca, Andrea Beatriz Juana
Kaufman, Teodoro Saul
author Pergomet, Jorgelina Leonor
author_facet Pergomet, Jorgelina Leonor
Bracca, Andrea Beatriz Juana
Kaufman, Teodoro Saul
author_role author
author2 Bracca, Andrea Beatriz Juana
Kaufman, Teodoro Saul
author2_role author
author
dc.subject.none.fl_str_mv PTEROPHYLLINES 2 AND 4
GERBERINOL I
CASNATI-SKATTEBOL
NATURAL PRODUCT SYNTHESIS
topic PTEROPHYLLINES 2 AND 4
GERBERINOL I
CASNATI-SKATTEBOL
NATURAL PRODUCT SYNTHESIS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The concise and efficient total syntheses of the naturally-occurring coumarin derivatives gerberinol I, and the pterophyllins 2 and 4, from 5-methyl-4-hydroxycoumarin as a common precursor employing different Casnati-Skattebøl reaction conditions, are reported. The synthesis of the key intermediate coumarin was achieved by the organocatalytic condensation of acetylacetone and crotonaldehyde followed by a LiCl-assisted cyclization, CuCl2-promoted aromatization and a final Et2CO3-mediated cyclization. A Casnati-Skattebøl formylation under high-temperature conditions afforded gerberinol I, whereas milder conditions resulted in an unstable 3-formyl-4-hydroxycoumarin derivative, which was subjected to a basic alumina-mediated one pot O-alkylation with chloroacetone and intramolecular aldolization to furnish pterophyllin 4. Wittig methylenation of the latter conveniently afforded pterophyllin 2.
Fil: Pergomet, Jorgelina Leonor. 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: Bracca, Andrea Beatriz Juana. 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: Kaufman, Teodoro Saul. 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 The concise and efficient total syntheses of the naturally-occurring coumarin derivatives gerberinol I, and the pterophyllins 2 and 4, from 5-methyl-4-hydroxycoumarin as a common precursor employing different Casnati-Skattebøl reaction conditions, are reported. The synthesis of the key intermediate coumarin was achieved by the organocatalytic condensation of acetylacetone and crotonaldehyde followed by a LiCl-assisted cyclization, CuCl2-promoted aromatization and a final Et2CO3-mediated cyclization. A Casnati-Skattebøl formylation under high-temperature conditions afforded gerberinol I, whereas milder conditions resulted in an unstable 3-formyl-4-hydroxycoumarin derivative, which was subjected to a basic alumina-mediated one pot O-alkylation with chloroacetone and intramolecular aldolization to furnish pterophyllin 4. Wittig methylenation of the latter conveniently afforded pterophyllin 2.
publishDate 2017
dc.date.none.fl_str_mv 2017-08
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/11336/63886
Pergomet, Jorgelina Leonor; Bracca, Andrea Beatriz Juana; Kaufman, Teodoro Saul; Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 15; 33; 8-2017; 7040-7049
1477-0520
CONICET Digital
CONICET
url http://hdl.handle.net/11336/63886
identifier_str_mv Pergomet, Jorgelina Leonor; Bracca, Andrea Beatriz Juana; Kaufman, Teodoro Saul; Total syntheses of gerberinol i and the pterophyllins 2 and 4 using the Casnati-Skattebøl reaction under different conditions; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 15; 33; 8-2017; 7040-7049
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/https://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB01471F
info:eu-repo/semantics/altIdentifier/doi/10.1039/C7OB01471F
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
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
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score 13.070432

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