Synthesis of (E)-4-bromo-3-methoxybut-3-en-2-one, the key fragment in the polyhydroxylated chain common to oscillariolide and phormidolides A-C

The terminal bromomethoxydiene (BMD) moiety of the polyhydroxylated chain present in phormidolides and oscillariolides has been synthesized for first time. Several strategies for the stereoselective synthesis of the 4-bromo-3-methoxybut-3-en-2-ones are described. Furthermore, a preliminary study to...

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Detalhes bibliográficos
Autores: Gil, Alejandro, Lamariano Merketegi, Janire, Lorente Crivillé, Adriana, Albericio Palomera, Fernando, Álvarez Domingo, Mercedes
Tipo de documento: artigo
Estado:Versión aceptada para publicación
Data de publicação:2016
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:2445/98695
Acesso em linha:https://hdl.handle.net/2445/98695
Access Level:Acceso aberto
Palavra-chave:Productes naturals
Síntesi asimètrica
Química orgànica
Natural products
Asymmetric synthesis
Organic chemistry
Descrição
Resumo:The terminal bromomethoxydiene (BMD) moiety of the polyhydroxylated chain present in phormidolides and oscillariolides has been synthesized for first time. Several strategies for the stereoselective synthesis of the 4-bromo-3-methoxybut-3-en-2-ones are described. Furthermore, a preliminary study to successfully introduce this fragment within the polyol chain and introduction of the fatty acid allowed corroborate the end structure of the polyol.