A convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-ones
| Autor: | Teodoro S. Kaufman, Sebastián Osvaldo Simonetti, Enrique L. Larghi |
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| Rok vydání: | 2016 |
| Předmět: |
Double bond
Metathesis Quinolones 010402 general chemistry 01 natural sciences Biochemistry chemistry.chemical_compound TOTAL SYNTHESIS Side chain Moiety Precursor of Peniprequinolone Natural Products Physical and Theoretical Chemistry BIOACTIVE HETEROCYCLES chemistry.chemical_classification Biological Products Molecular Structure 010405 organic chemistry Chemistry Otras Ciencias Químicas Aryl Organic Chemistry Ciencias Químicas Penicillium Total synthesis Bioactive 6-substituted 5-hydroxy4-aryl-1H-quinolin-2-ones QUINOLONE Combinatorial chemistry 0104 chemical sciences Claisen rearrangement Aspergillus Wittig reaction CIENCIAS NATURALES Y EXACTAS |
| Zdroj: | RepHipUNR (UNR) Universidad Nacional de Rosario instacron:UNR |
| ISSN: | 1477-0539 |
| Popis: | 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. Fil: Simonetti, Sebastián Osvaldo. 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: 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 |
| Databáze: | OpenAIRE |
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