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...
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Formato: | article artículo publishedVersion |
Lenguaje: | Inglés |
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Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | http://hdl.handle.net/2133/10489 http://hdl.handle.net/2133/10489 |
Aporte de: |
id |
I15-R121-2133-10489 |
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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 |
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bdutipo_str |
Repositorios |
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1764820408420270080 |