Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol

Autores
Socolsky, Cecilia; Plietker, Bernd
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A short total synthesis of (±)-garcinol and (±)-isogarcinol, two endo-type B PPAPs with reported activity against methiciline resistant Staphylococcus aureus (MRSA), is presented. The separation of framework-constructing from framework-decorating steps and the application of two highly regio- and stereoselective Pd-catalysed allylations, that is, the Pd-catalysed decarboxylative Tsuji-Trost allylation and the diastereoselective Pd-catalysed allyl-allyl cross-coupling, are key elements that allowed the total synthesis to be accomplished within 13 steps starting from acetylacetone. After separation of the enantiomers the absolute configurations of the four natural products (i.e., (-)-garcinol, (+)-guttiferone E (i.e., ent-garcinol), (-)-isogarcinol, and (+)-isoxanthochymol (i.e., ent-isogarcinol)) were assigned based on ECD spectroscopy.
Fil: Socolsky, Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; Argentina
Fil: Plietker, Bernd . Universität Stuttgart. Institut für Organische Chemie; Alemania
Materia
ALLYLATION
ANTIBIOTICS
CATALYSIS
CROSS-COUPLING
NATURAL PRODUCTS
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:11336/6926
Acceder
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network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinolSocolsky, CeciliaPlietker, BerndALLYLATIONANTIBIOTICSCATALYSISCROSS-COUPLINGNATURAL PRODUCTShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A short total synthesis of (±)-garcinol and (±)-isogarcinol, two endo-type B PPAPs with reported activity against methiciline resistant Staphylococcus aureus (MRSA), is presented. The separation of framework-constructing from framework-decorating steps and the application of two highly regio- and stereoselective Pd-catalysed allylations, that is, the Pd-catalysed decarboxylative Tsuji-Trost allylation and the diastereoselective Pd-catalysed allyl-allyl cross-coupling, are key elements that allowed the total synthesis to be accomplished within 13 steps starting from acetylacetone. After separation of the enantiomers the absolute configurations of the four natural products (i.e., (-)-garcinol, (+)-guttiferone E (i.e., ent-garcinol), (-)-isogarcinol, and (+)-isoxanthochymol (i.e., ent-isogarcinol)) were assigned based on ECD spectroscopy.Fil: Socolsky, Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; ArgentinaFil: Plietker, Bernd . Universität Stuttgart. Institut für Organische Chemie; AlemaniaWiley2014-12-23info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6926Socolsky, Cecilia; Plietker, Bernd ; Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol; Wiley; Chemistry- A European Journal; 21; 7; 23-12-2014; 3053–30610947-65391521-3765enginfo:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201406077info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chem.201406077/abstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:15:55Zoai:ri.conicet.gov.ar:11336/6926instacron: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 10:15:55.638CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol
title Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol
spellingShingle Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol
Socolsky, Cecilia
ALLYLATION
ANTIBIOTICS
CATALYSIS
CROSS-COUPLING
NATURAL PRODUCTS
title_short Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol
title_full Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol
title_fullStr Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol
title_full_unstemmed Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol
title_sort Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol
dc.creator.none.fl_str_mv Socolsky, Cecilia
Plietker, Bernd
author Socolsky, Cecilia
author_facet Socolsky, Cecilia
Plietker, Bernd
author_role author
author2 Plietker, Bernd
author2_role author
dc.subject.none.fl_str_mv ALLYLATION
ANTIBIOTICS
CATALYSIS
CROSS-COUPLING
NATURAL PRODUCTS
topic ALLYLATION
ANTIBIOTICS
CATALYSIS
CROSS-COUPLING
NATURAL PRODUCTS
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 short total synthesis of (±)-garcinol and (±)-isogarcinol, two endo-type B PPAPs with reported activity against methiciline resistant Staphylococcus aureus (MRSA), is presented. The separation of framework-constructing from framework-decorating steps and the application of two highly regio- and stereoselective Pd-catalysed allylations, that is, the Pd-catalysed decarboxylative Tsuji-Trost allylation and the diastereoselective Pd-catalysed allyl-allyl cross-coupling, are key elements that allowed the total synthesis to be accomplished within 13 steps starting from acetylacetone. After separation of the enantiomers the absolute configurations of the four natural products (i.e., (-)-garcinol, (+)-guttiferone E (i.e., ent-garcinol), (-)-isogarcinol, and (+)-isoxanthochymol (i.e., ent-isogarcinol)) were assigned based on ECD spectroscopy.
Fil: Socolsky, Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; Argentina
Fil: Plietker, Bernd . Universität Stuttgart. Institut für Organische Chemie; Alemania
description A short total synthesis of (±)-garcinol and (±)-isogarcinol, two endo-type B PPAPs with reported activity against methiciline resistant Staphylococcus aureus (MRSA), is presented. The separation of framework-constructing from framework-decorating steps and the application of two highly regio- and stereoselective Pd-catalysed allylations, that is, the Pd-catalysed decarboxylative Tsuji-Trost allylation and the diastereoselective Pd-catalysed allyl-allyl cross-coupling, are key elements that allowed the total synthesis to be accomplished within 13 steps starting from acetylacetone. After separation of the enantiomers the absolute configurations of the four natural products (i.e., (-)-garcinol, (+)-guttiferone E (i.e., ent-garcinol), (-)-isogarcinol, and (+)-isoxanthochymol (i.e., ent-isogarcinol)) were assigned based on ECD spectroscopy.
publishDate 2014
dc.date.none.fl_str_mv 2014-12-23
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/11336/6926
Socolsky, Cecilia; Plietker, Bernd ; Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol; Wiley; Chemistry- A European Journal; 21; 7; 23-12-2014; 3053–3061
0947-6539
1521-3765
url http://hdl.handle.net/11336/6926
identifier_str_mv Socolsky, Cecilia; Plietker, Bernd ; Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol; Wiley; Chemistry- A European Journal; 21; 7; 23-12-2014; 3053–3061
0947-6539
1521-3765
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201406077
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chem.201406077/abstract
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
publisher.none.fl_str_mv Wiley
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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