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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/127117
Ver los metadatos del registro completo
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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 Técnicas2025-09-03T09:58:19Zoai: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:34982025-09-03 09:58:19.422CONICET 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 |
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1842269515661967360 |
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13.13397 |