Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H

Autores
Della Felice, Franco; Sarotti, Ariel Marcelo; Pilli, Ronaldo A.
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The total synthesis and structural revision of (+)-cryptoconcatone H are described. Guided by computational studies for the final structure assignment, the stereogenic centers at the tetrahydropyran moiety of (+)-cryptoconcatone H were assembled through catalytic asymmetric methodologies: Krische allylation, cross-metathesis reaction, and THP formation via Pd(II)-catalyzed cyclization. Finally, a Krische allylation reaction established the last stereocenter, and the lactone moiety was formed by ring-closing metathesis.
Fil: Della Felice, Franco. Universidade Estadual de Campinas; Brasil
Fil: Sarotti, Ariel Marcelo. 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: Pilli, Ronaldo A.. Universidade Estadual de Campinas; Brasil
Materia
CATALYTIC ASYMMETRIC SYNTHESIS
STEREOCHEMICAL REVISION
CRYPTOCONCATONE H
DP4+ CALCULATIONS
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:11336/53198
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/53198
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone HDella Felice, FrancoSarotti, Ariel MarceloPilli, Ronaldo A.CATALYTIC ASYMMETRIC SYNTHESISSTEREOCHEMICAL REVISIONCRYPTOCONCATONE HDP4+ CALCULATIONShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The total synthesis and structural revision of (+)-cryptoconcatone H are described. Guided by computational studies for the final structure assignment, the stereogenic centers at the tetrahydropyran moiety of (+)-cryptoconcatone H were assembled through catalytic asymmetric methodologies: Krische allylation, cross-metathesis reaction, and THP formation via Pd(II)-catalyzed cyclization. Finally, a Krische allylation reaction established the last stereocenter, and the lactone moiety was formed by ring-closing metathesis.Fil: Della Felice, Franco. Universidade Estadual de Campinas; BrasilFil: Sarotti, Ariel Marcelo. 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: Pilli, Ronaldo A.. Universidade Estadual de Campinas; BrasilAmerican Chemical Society2017-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/53198Della Felice, Franco; Sarotti, Ariel Marcelo; Pilli, Ronaldo A.; Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H; American Chemical Society; Journal of Organic Chemistry; 82; 17; 9-2017; 9191-91970022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.7b01378info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.7b01378info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:59:05Zoai:ri.conicet.gov.ar:11336/53198instacron: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:34982025-11-12 09:59:06.275CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H
title Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H
spellingShingle Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H
Della Felice, Franco
CATALYTIC ASYMMETRIC SYNTHESIS
STEREOCHEMICAL REVISION
CRYPTOCONCATONE H
DP4+ CALCULATIONS
title_short Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H
title_full Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H
title_fullStr Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H
title_full_unstemmed Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H
title_sort Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H
dc.creator.none.fl_str_mv Della Felice, Franco
Sarotti, Ariel Marcelo
Pilli, Ronaldo A.
author Della Felice, Franco
author_facet Della Felice, Franco
Sarotti, Ariel Marcelo
Pilli, Ronaldo A.
author_role author
author2 Sarotti, Ariel Marcelo
Pilli, Ronaldo A.
author2_role author
author
dc.subject.none.fl_str_mv CATALYTIC ASYMMETRIC SYNTHESIS
STEREOCHEMICAL REVISION
CRYPTOCONCATONE H
DP4+ CALCULATIONS
topic CATALYTIC ASYMMETRIC SYNTHESIS
STEREOCHEMICAL REVISION
CRYPTOCONCATONE H
DP4+ CALCULATIONS
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 total synthesis and structural revision of (+)-cryptoconcatone H are described. Guided by computational studies for the final structure assignment, the stereogenic centers at the tetrahydropyran moiety of (+)-cryptoconcatone H were assembled through catalytic asymmetric methodologies: Krische allylation, cross-metathesis reaction, and THP formation via Pd(II)-catalyzed cyclization. Finally, a Krische allylation reaction established the last stereocenter, and the lactone moiety was formed by ring-closing metathesis.
Fil: Della Felice, Franco. Universidade Estadual de Campinas; Brasil
Fil: Sarotti, Ariel Marcelo. 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: Pilli, Ronaldo A.. Universidade Estadual de Campinas; Brasil
description The total synthesis and structural revision of (+)-cryptoconcatone H are described. Guided by computational studies for the final structure assignment, the stereogenic centers at the tetrahydropyran moiety of (+)-cryptoconcatone H were assembled through catalytic asymmetric methodologies: Krische allylation, cross-metathesis reaction, and THP formation via Pd(II)-catalyzed cyclization. Finally, a Krische allylation reaction established the last stereocenter, and the lactone moiety was formed by ring-closing metathesis.
publishDate 2017
dc.date.none.fl_str_mv 2017-09
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/11336/53198
Della Felice, Franco; Sarotti, Ariel Marcelo; Pilli, Ronaldo A.; Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H; American Chemical Society; Journal of Organic Chemistry; 82; 17; 9-2017; 9191-9197
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/53198
identifier_str_mv Della Felice, Franco; Sarotti, Ariel Marcelo; Pilli, Ronaldo A.; Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H; American Chemical Society; Journal of Organic Chemistry; 82; 17; 9-2017; 9191-9197
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.7b01378
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.7b01378
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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 12.976206

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