Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids

Autores
Ventosa Andrés, Pilar; la Venia, Agustina; Ripoll, Carlos Alfonso Barea; Hradilová, Ludmila; Krchnak, Viktor
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Herein, we describe the synthesis of molecular scaffolds consisting of medium-sized fused heterocycles using amino acids, which are some of the most useful building blocks used by nature as well as chemists to create structural diversity. The acyclic precursors were assembled by using traditional Merrifield solid-phase peptide synthesis, and cyclization was carried out through acid-mediated tandem endocyclic N-acyliminium ion formation, followed by nucleophilic addition with internal nucleophiles. The synthesis of molecular scaffolds consisting of seven-, eight-, and nine-membered rings proceeded with full stereocontrol of the newly generated stereogenic center in most cases.
Fil: Ventosa Andrés, Pilar. Palacky University; República Checa
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Palacky University; República Checa
Fil: Ripoll, Carlos Alfonso Barea. Palacky University; República Checa
Fil: Hradilová, Ludmila. Farmak; República Checa
Fil: Krchnak, Viktor. Palacky University; República Checa. University of Notre Dame; Estados Unidos
Materia
Cyclization
Drug Discovery
Fused-Ring Systems
Regioselectivity
Solid-Phase 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:11336/52782
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/52782
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino AcidsVentosa Andrés, Pilarla Venia, AgustinaRipoll, Carlos Alfonso BareaHradilová, LudmilaKrchnak, ViktorCyclizationDrug DiscoveryFused-Ring SystemsRegioselectivitySolid-Phase Synthesishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Herein, we describe the synthesis of molecular scaffolds consisting of medium-sized fused heterocycles using amino acids, which are some of the most useful building blocks used by nature as well as chemists to create structural diversity. The acyclic precursors were assembled by using traditional Merrifield solid-phase peptide synthesis, and cyclization was carried out through acid-mediated tandem endocyclic N-acyliminium ion formation, followed by nucleophilic addition with internal nucleophiles. The synthesis of molecular scaffolds consisting of seven-, eight-, and nine-membered rings proceeded with full stereocontrol of the newly generated stereogenic center in most cases.Fil: Ventosa Andrés, Pilar. Palacky University; República ChecaFil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Palacky University; República ChecaFil: Ripoll, Carlos Alfonso Barea. Palacky University; República ChecaFil: Hradilová, Ludmila. Farmak; República ChecaFil: Krchnak, Viktor. Palacky University; República Checa. University of Notre Dame; Estados UnidosWiley VCH Verlag2015-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/52782Ventosa Andrés, Pilar; la Venia, Agustina; Ripoll, Carlos Alfonso Barea; Hradilová, Ludmila; Krchnak, Viktor; Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids; Wiley VCH Verlag; Chemistry- A European Journal; 21; 37; 9-2015; 13112-131190947-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201501746info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201501746info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:25:52Zoai:ri.conicet.gov.ar:11336/52782instacron: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 10:25:52.672CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids
title Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids
spellingShingle Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids
Ventosa Andrés, Pilar
Cyclization
Drug Discovery
Fused-Ring Systems
Regioselectivity
Solid-Phase Synthesis
title_short Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids
title_full Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids
title_fullStr Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids
title_full_unstemmed Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids
title_sort Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids
dc.creator.none.fl_str_mv Ventosa Andrés, Pilar
la Venia, Agustina
Ripoll, Carlos Alfonso Barea
Hradilová, Ludmila
Krchnak, Viktor
author Ventosa Andrés, Pilar
author_facet Ventosa Andrés, Pilar
la Venia, Agustina
Ripoll, Carlos Alfonso Barea
Hradilová, Ludmila
Krchnak, Viktor
author_role author
author2 la Venia, Agustina
Ripoll, Carlos Alfonso Barea
Hradilová, Ludmila
Krchnak, Viktor
author2_role author
author
author
author
dc.subject.none.fl_str_mv Cyclization
Drug Discovery
Fused-Ring Systems
Regioselectivity
Solid-Phase Synthesis
topic Cyclization
Drug Discovery
Fused-Ring Systems
Regioselectivity
Solid-Phase 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 Herein, we describe the synthesis of molecular scaffolds consisting of medium-sized fused heterocycles using amino acids, which are some of the most useful building blocks used by nature as well as chemists to create structural diversity. The acyclic precursors were assembled by using traditional Merrifield solid-phase peptide synthesis, and cyclization was carried out through acid-mediated tandem endocyclic N-acyliminium ion formation, followed by nucleophilic addition with internal nucleophiles. The synthesis of molecular scaffolds consisting of seven-, eight-, and nine-membered rings proceeded with full stereocontrol of the newly generated stereogenic center in most cases.
Fil: Ventosa Andrés, Pilar. Palacky University; República Checa
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Palacky University; República Checa
Fil: Ripoll, Carlos Alfonso Barea. Palacky University; República Checa
Fil: Hradilová, Ludmila. Farmak; República Checa
Fil: Krchnak, Viktor. Palacky University; República Checa. University of Notre Dame; Estados Unidos
description Herein, we describe the synthesis of molecular scaffolds consisting of medium-sized fused heterocycles using amino acids, which are some of the most useful building blocks used by nature as well as chemists to create structural diversity. The acyclic precursors were assembled by using traditional Merrifield solid-phase peptide synthesis, and cyclization was carried out through acid-mediated tandem endocyclic N-acyliminium ion formation, followed by nucleophilic addition with internal nucleophiles. The synthesis of molecular scaffolds consisting of seven-, eight-, and nine-membered rings proceeded with full stereocontrol of the newly generated stereogenic center in most cases.
publishDate 2015
dc.date.none.fl_str_mv 2015-09
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/11336/52782
Ventosa Andrés, Pilar; la Venia, Agustina; Ripoll, Carlos Alfonso Barea; Hradilová, Ludmila; Krchnak, Viktor; Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids; Wiley VCH Verlag; Chemistry- A European Journal; 21; 37; 9-2015; 13112-13119
0947-6539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/52782
identifier_str_mv Ventosa Andrés, Pilar; la Venia, Agustina; Ripoll, Carlos Alfonso Barea; Hradilová, Ludmila; Krchnak, Viktor; Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids; Wiley VCH Verlag; Chemistry- A European Journal; 21; 37; 9-2015; 13112-13119
0947-6539
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201501746
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201501746
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 VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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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