A gram-scale route to phlegmarine alkaloids: rapid total synthesis of (-)-cermizine B

The synthesis of the Lycopodium alkaloid ( )-cermizine B (1), which establishes its absolute configuration, is achieved by combining asymmetric organocatalysis and an uninterrupted eight-step reaction sequence, followed by a final reduction step. This ''pot-economy'' strategy pro...

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Detalles Bibliográficos
Autores: Bradshaw, Ben, Luque Corredera, Carlos, Bonjoch i Sesé, Josep
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2014
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/225192
Acceso en línea:https://hdl.handle.net/2445/225192
Access Level:acceso abierto
Palabra clave:Medicaments
Alcaloides
Síntesi orgànica
Drugs
Alkaloids
Organic synthesis
Descripción
Sumario:The synthesis of the Lycopodium alkaloid ( )-cermizine B (1), which establishes its absolute configuration, is achieved by combining asymmetric organocatalysis and an uninterrupted eight-step reaction sequence, followed by a final reduction step. This ''pot-economy'' strategy provides access to the cis-phlegmarine stereo parent embedded in 1 for the first time, rapidly and on a gram-scale.