Synthesis of limonoid CDE fragments related to limonin and nimbinim

[EN]A practical, brief and selective synthesis of limonoid CDE fragments from a readily available starting diketone is described. The key step is a cationic electrocyclization promoted by strong acids. In general the methodology has been demonstrated for compounds with sensitive furane and thiophene...

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Detalhes bibliográficos
Autores: Simmonds, M.S.J., Fernández Mateos, Alfonso, Herrero Teijón, Pablo, Pascual Coca, Gustavo, Rubio González, María Rosa
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2010
País:España
Recursos:Universidad de Salamanca (USAL)
Repositorio:GREDOS. Repositorio Institucional de la Universidad de Salamanca
OAI Identifier:oai:gredos.usal.es:10366/154181
Acesso em linha:http://hdl.handle.net/10366/154181
Access Level:acceso abierto
Palavra-chave:Limonoids
Nazarov cyclization
Antifeedant
Nimbinim
Limonim
2306 Química Orgánica
Descrição
Resumo:[EN]A practical, brief and selective synthesis of limonoid CDE fragments from a readily available starting diketone is described. The key step is a cationic electrocyclization promoted by strong acids. In general the methodology has been demonstrated for compounds with sensitive furane and thiophene substituents to obtain diverse substituted indenones. Several of the compounds obtained show significant antifeedant activity against Spodoptera littoralis.