Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects

Autores
Larghi, Enrique Leandro; Kaufman, Teodoro Saul
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The oxa-Pictet-Spengler cyclization is the oxygen variation of the Pictet-Spengler reaction, in which an aromatic alcohol component (generally a β-arylethyl alcohol) reacts with acarbonyl component (aldehyde, ketone or their masked derivatives), to yield a 1-substituted (or 1,1′- disubstituted)pyran fused to the aromatic ring system found in the starting alcohol. The transformation is usually promoted by Brønsted and Lewis acids. Intramolecular versions of the reaction are also known, where both components are mutually masked as an acetal. Discussed here are aspects concerning the most recent developments and new applications of this useful reaction, including the scope and limitations of new promoters, and new mechanistic pictures of this transformation. The use of novel stereochemical control strategies and the application of the reaction to the synthesis of natural products and their analogs, as well as to accessing fully synthetic bioactive compounds and new ring systems are presented, and chiral versions of the oxa-Pictet-Spengler are also analyzed.
Fil: Larghi, Enrique Leandro. 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: Kaufman, Teodoro Saul. 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
Materia
CYCLIZATION
NATURAL PRODUCTS
OXYGEN HETEROCYCLES
SYNTHESIS DESIGN
SYNTHETIC METHODS
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:11336/127117
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New ProspectsLarghi, Enrique LeandroKaufman, Teodoro SaulCYCLIZATIONNATURAL PRODUCTSOXYGEN HETEROCYCLESSYNTHESIS DESIGNSYNTHETIC METHODShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The oxa-Pictet-Spengler cyclization is the oxygen variation of the Pictet-Spengler reaction, in which an aromatic alcohol component (generally a β-arylethyl alcohol) reacts with acarbonyl component (aldehyde, ketone or their masked derivatives), to yield a 1-substituted (or 1,1′- disubstituted)pyran fused to the aromatic ring system found in the starting alcohol. The transformation is usually promoted by Brønsted and Lewis acids. Intramolecular versions of the reaction are also known, where both components are mutually masked as an acetal. Discussed here are aspects concerning the most recent developments and new applications of this useful reaction, including the scope and limitations of new promoters, and new mechanistic pictures of this transformation. The use of novel stereochemical control strategies and the application of the reaction to the synthesis of natural products and their analogs, as well as to accessing fully synthetic bioactive compounds and new ring systems are presented, and chiral versions of the oxa-Pictet-Spengler are also analyzed.Fil: Larghi, Enrique Leandro. 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: Kaufman, Teodoro Saul. 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; ArgentinaWiley VCH Verlag2011-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/127117Larghi, Enrique Leandro; Kaufman, Teodoro Saul; Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects; Wiley VCH Verlag; European Journal of Organic Chemistry; 27; 9-2011; 5195-52311434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201100271info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201100271info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:05:56Zoai:ri.conicet.gov.ar:11336/127117instacron: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 10:05:57.226CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects
title Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects
spellingShingle Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects
Larghi, Enrique Leandro
CYCLIZATION
NATURAL PRODUCTS
OXYGEN HETEROCYCLES
SYNTHESIS DESIGN
SYNTHETIC METHODS
title_short Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects
title_full Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects
title_fullStr Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects
title_full_unstemmed Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects
title_sort Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects
dc.creator.none.fl_str_mv Larghi, Enrique Leandro
Kaufman, Teodoro Saul
author Larghi, Enrique Leandro
author_facet Larghi, Enrique Leandro
Kaufman, Teodoro Saul
author_role author
author2 Kaufman, Teodoro Saul
author2_role author
dc.subject.none.fl_str_mv CYCLIZATION
NATURAL PRODUCTS
OXYGEN HETEROCYCLES
SYNTHESIS DESIGN
SYNTHETIC METHODS
topic CYCLIZATION
NATURAL PRODUCTS
OXYGEN HETEROCYCLES
SYNTHESIS DESIGN
SYNTHETIC METHODS
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 oxa-Pictet-Spengler cyclization is the oxygen variation of the Pictet-Spengler reaction, in which an aromatic alcohol component (generally a β-arylethyl alcohol) reacts with acarbonyl component (aldehyde, ketone or their masked derivatives), to yield a 1-substituted (or 1,1′- disubstituted)pyran fused to the aromatic ring system found in the starting alcohol. The transformation is usually promoted by Brønsted and Lewis acids. Intramolecular versions of the reaction are also known, where both components are mutually masked as an acetal. Discussed here are aspects concerning the most recent developments and new applications of this useful reaction, including the scope and limitations of new promoters, and new mechanistic pictures of this transformation. The use of novel stereochemical control strategies and the application of the reaction to the synthesis of natural products and their analogs, as well as to accessing fully synthetic bioactive compounds and new ring systems are presented, and chiral versions of the oxa-Pictet-Spengler are also analyzed.
Fil: Larghi, Enrique Leandro. 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: Kaufman, Teodoro Saul. 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
description The oxa-Pictet-Spengler cyclization is the oxygen variation of the Pictet-Spengler reaction, in which an aromatic alcohol component (generally a β-arylethyl alcohol) reacts with acarbonyl component (aldehyde, ketone or their masked derivatives), to yield a 1-substituted (or 1,1′- disubstituted)pyran fused to the aromatic ring system found in the starting alcohol. The transformation is usually promoted by Brønsted and Lewis acids. Intramolecular versions of the reaction are also known, where both components are mutually masked as an acetal. Discussed here are aspects concerning the most recent developments and new applications of this useful reaction, including the scope and limitations of new promoters, and new mechanistic pictures of this transformation. The use of novel stereochemical control strategies and the application of the reaction to the synthesis of natural products and their analogs, as well as to accessing fully synthetic bioactive compounds and new ring systems are presented, and chiral versions of the oxa-Pictet-Spengler are also analyzed.
publishDate 2011
dc.date.none.fl_str_mv 2011-09
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/11336/127117
Larghi, Enrique Leandro; Kaufman, Teodoro Saul; Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects; Wiley VCH Verlag; European Journal of Organic Chemistry; 27; 9-2011; 5195-5231
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/127117
identifier_str_mv Larghi, Enrique Leandro; Kaufman, Teodoro Saul; Synthesis of Oxacycles Employing the Oxa-Pictet–Spengler Reaction: Recent Developments and New Prospects; Wiley VCH Verlag; European Journal of Organic Chemistry; 27; 9-2011; 5195-5231
1434-193X
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://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201100271
info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201100271
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
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
_version_ 1844613901563461632
score 13.070432

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