Modular total syntheses of thymifodioic/incanic acids

The first total synthesis of the bioactive natural product 2,6-(E,E)-thymifodioic acid, also called incanic acid, and its stereoisomers is described. An unified, iterative and modular strategy was envisioned, achieving the synthesis of the goals products after five reaction steps in an overall yield...

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Detalhes bibliográficos
Autores: Álvarez Méndez, Sergio J., Saad, José Roberto, Tonn, Carlos Eugenio, Martín, Víctor S., García, Celina
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:2019
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositório:CONICET Digital (CONICET)
Idioma:inglês
OAI Identifier:oai:ri.conicet.gov.ar:11336/144258
Acesso em linha:http://hdl.handle.net/11336/144258
Access Level:Acceso aberto
Palavra-chave:ITERATIVE SYNTHESIS
NATURAL PRODUCTS
OLEFINATION
TERPENES
TOTAL SYNTHESIS
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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spelling Modular total syntheses of thymifodioic/incanic acidsÁlvarez Méndez, Sergio J.Saad, José RobertoTonn, Carlos EugenioMartín, Víctor S.García, CelinaITERATIVE SYNTHESISNATURAL PRODUCTSOLEFINATIONTERPENESTOTAL SYNTHESIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The first total synthesis of the bioactive natural product 2,6-(E,E)-thymifodioic acid, also called incanic acid, and its stereoisomers is described. An unified, iterative and modular strategy was envisioned, achieving the synthesis of the goals products after five reaction steps in an overall yield ranging from 8% to 16%. The key step is a non-expensive easy to perform Horner–Wadsworth–Emmons condensation.Fil: Álvarez Méndez, Sergio J.. Universidad de la Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; EspañaFil: Saad, José Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Martín, Víctor S.. Universidad de la Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; EspañaFil: García, Celina. Universidad de la Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; EspañaElsevier2019-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/144258Álvarez Méndez, Sergio J.; Saad, José Roberto; Tonn, Carlos Eugenio; Martín, Víctor S.; García, Celina; Modular total syntheses of thymifodioic/incanic acids; Elsevier; Arabian Journal of Chemistry; 12; 8; 12-2019; 3764-37751878-5352CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1878535216000095info:eu-repo/semantics/altIdentifier/doi/10.1016/j.arabjc.2016.01.008info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T14:09:45Zoai:ri.conicet.gov.ar:11336/144258instacron: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:34982024-05-08 14:09:45.571CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Modular total syntheses of thymifodioic/incanic acids
title Modular total syntheses of thymifodioic/incanic acids
spellingShingle Modular total syntheses of thymifodioic/incanic acids
Álvarez Méndez, Sergio J.
ITERATIVE SYNTHESIS
NATURAL PRODUCTS
OLEFINATION
TERPENES
TOTAL SYNTHESIS
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Modular total syntheses of thymifodioic/incanic acids
title_full Modular total syntheses of thymifodioic/incanic acids
title_fullStr Modular total syntheses of thymifodioic/incanic acids
title_full_unstemmed Modular total syntheses of thymifodioic/incanic acids
title_sort Modular total syntheses of thymifodioic/incanic acids
dc.creator.none.fl_str_mv Álvarez Méndez, Sergio J.
Saad, José Roberto
Tonn, Carlos Eugenio
Martín, Víctor S.
García, Celina
author Álvarez Méndez, Sergio J.
author_facet Álvarez Méndez, Sergio J.
Saad, José Roberto
Tonn, Carlos Eugenio
Martín, Víctor S.
García, Celina
author_role author
author2 Saad, José Roberto
Tonn, Carlos Eugenio
Martín, Víctor S.
García, Celina
author2_role author
author
author
author
dc.subject.none.fl_str_mv ITERATIVE SYNTHESIS
NATURAL PRODUCTS
OLEFINATION
TERPENES
TOTAL SYNTHESIS
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic ITERATIVE SYNTHESIS
NATURAL PRODUCTS
OLEFINATION
TERPENES
TOTAL SYNTHESIS
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description The first total synthesis of the bioactive natural product 2,6-(E,E)-thymifodioic acid, also called incanic acid, and its stereoisomers is described. An unified, iterative and modular strategy was envisioned, achieving the synthesis of the goals products after five reaction steps in an overall yield ranging from 8% to 16%. The key step is a non-expensive easy to perform Horner–Wadsworth–Emmons condensation.
publishDate 2019
dc.date.none.fl_str_mv 2019-12
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/11336/144258
Álvarez Méndez, Sergio J.; Saad, José Roberto; Tonn, Carlos Eugenio; Martín, Víctor S.; García, Celina; Modular total syntheses of thymifodioic/incanic acids; Elsevier; Arabian Journal of Chemistry; 12; 8; 12-2019; 3764-3775
1878-5352
CONICET Digital
CONICET
url http://hdl.handle.net/11336/144258
identifier_str_mv Álvarez Méndez, Sergio J.; Saad, José Roberto; Tonn, Carlos Eugenio; Martín, Víctor S.; García, Celina; Modular total syntheses of thymifodioic/incanic acids; Elsevier; Arabian Journal of Chemistry; 12; 8; 12-2019; 3764-3775
1878-5352
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://www.sciencedirect.com/science/article/pii/S1878535216000095
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.arabjc.2016.01.008
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
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
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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 15,198674

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