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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/53198
Ver los metadatos del registro completo
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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 Técnicas2025-09-29T10:42:57Zoai: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:34982025-09-29 10:42:57.698CONICET 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 |
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CONICET Digital (CONICET) |
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CONICET Digital (CONICET) |
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Consejo Nacional de Investigaciones Científicas y Técnicas |
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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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1844614463419842560 |
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13.070432 |