A convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-ones

5-Hydroxy-4-aryl-3,4-dihydro-1H-quinolin-2-ones are a small family of natural products isolated from fungal strains of Penicillium and Aspergillus. Most of its members, which are insecticides and anthelmintics, carry an isoprenoid C-6 side chain. The synthesis of a 6-propenyl-substituted advanced...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Simonetti, Sebastián Osvaldo, Larghi, Enrique Leandro, Kaufman, Teodoro Saúl
Formato: article artículo publishedVersion
Lenguaje:Inglés
Publicado: Royal Society of Chemistry 2018
Materias:
Bioactive 6-substituted 5-hydroxy4-aryl-1H-quinolin-2-ones
Natural Products
Metathesis
Precursor of Peniprequinolone
Acceso en línea:http://hdl.handle.net/2133/10489
http://hdl.handle.net/2133/10489
Aporte de:
Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario
id I15-R121-2133-10489
record_format dspace
institution Universidad Nacional de Rosario
institution_str I-15
repository_str R-121
collection Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR)
language Inglés
orig_language_str_mv eng
topic Bioactive 6-substituted 5-hydroxy4-aryl-1H-quinolin-2-ones
Natural Products
Metathesis
Precursor of Peniprequinolone
spellingShingle Bioactive 6-substituted 5-hydroxy4-aryl-1H-quinolin-2-ones
Natural Products
Metathesis
Precursor of Peniprequinolone
Simonetti, Sebastián Osvaldo
Larghi, Enrique Leandro
Kaufman, Teodoro Saúl
A convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-ones
topic_facet Bioactive 6-substituted 5-hydroxy4-aryl-1H-quinolin-2-ones
Natural Products
Metathesis
Precursor of Peniprequinolone
description 5-Hydroxy-4-aryl-3,4-dihydro-1H-quinolin-2-ones are a small family of natural products isolated from fungal strains of Penicillium and Aspergillus. Most of its members, which are insecticides and anthelmintics, carry an isoprenoid C-6 side chain. The synthesis of a 6-propenyl-substituted advanced intermediate for the total synthesis of these natural products is presented in this paper. This was achieved through the stereoselective construction of a β,β-diarylacrylate derivative from 6-nitrosalicylaldehyde, using a Wittig olefination and a Heck–Matsuda arylation, followed by a selective Fe0-mediated reductive cyclization. Installation of the 6-propenyl side chain was performed by 5-O-allylation of the heterocycle, followed by Claisen rearrangement and conjugative migration of the allyl double bond, as the key steps. The Grubbs II-catalyzed olefin cross metathesis of the 6-allyl moiety with 2-methylbut-2-ene to afford a precursor of peniprequinolone is also reported.
format article
artículo
publishedVersion
author Simonetti, Sebastián Osvaldo
Larghi, Enrique Leandro
Kaufman, Teodoro Saúl
author_facet Simonetti, Sebastián Osvaldo
Larghi, Enrique Leandro
Kaufman, Teodoro Saúl
author_sort Simonetti, Sebastián Osvaldo
title A convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-ones
title_short A convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-ones
title_full A convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-ones
title_fullStr A convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-ones
title_full_unstemmed A convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-ones
title_sort convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1h-quinolin-2-ones
publisher Royal Society of Chemistry
publishDate 2018
url http://hdl.handle.net/2133/10489
http://hdl.handle.net/2133/10489
work_keys_str_mv AT simonettisebastianosvaldo aconvenientapproachtoanadvancedintermediatetowardthenaturallyoccurringbioactive6substituted5hydroxy4aryl1hquinolin2ones
AT larghienriqueleandro aconvenientapproachtoanadvancedintermediatetowardthenaturallyoccurringbioactive6substituted5hydroxy4aryl1hquinolin2ones
AT kaufmanteodorosaul aconvenientapproachtoanadvancedintermediatetowardthenaturallyoccurringbioactive6substituted5hydroxy4aryl1hquinolin2ones
AT simonettisebastianosvaldo convenientapproachtoanadvancedintermediatetowardthenaturallyoccurringbioactive6substituted5hydroxy4aryl1hquinolin2ones
AT larghienriqueleandro convenientapproachtoanadvancedintermediatetowardthenaturallyoccurringbioactive6substituted5hydroxy4aryl1hquinolin2ones
AT kaufmanteodorosaul convenientapproachtoanadvancedintermediatetowardthenaturallyoccurringbioactive6substituted5hydroxy4aryl1hquinolin2ones
bdutipo_str Repositorios
_version_ 1764820408420270080

Ejemplares similares