A synthetic approach to ervatamine-silicine alkaloids. Enantioselective total synthesis of (-)-episilicine

Starting from an appropriate unsaturated phenylglycinol-derived oxazolopiperidone lactam, the synthesis of (-)-16-episilicine is reported, the key steps being a stereoselective conjugate addition, a stereoselective alkylation, and a ring-closing metathesis reaction. This represents the first enantio...

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Detalhes bibliográficos
Autores: Amat Tusón, Mercedes, Llor Brunés, Núria, Checa Castaño, Begoña, Molins i Grau, Elies, Bosch Cartes, Joan
Tipo de documento: artigo
Estado:Versión aceptada para publicación
Data de publicação:2010
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositório:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/164358
Acesso em linha:https://hdl.handle.net/2445/164358
Access Level:Acceso aberto
Palavra-chave:Alcaloides
Lactames
Síntesi asimètrica
Alkaloids
Lactams
Asymmetric synthesis
Descrição
Resumo:Starting from an appropriate unsaturated phenylglycinol-derived oxazolopiperidone lactam, the synthesis of (-)-16-episilicine is reported, the key steps being a stereoselective conjugate addition, a stereoselective alkylation, and a ring-closing metathesis reaction. This represents the first enantioselective total synthesis of an alkaloid of the silicine group.