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Síntesis total de lucilactaeno, un inhibidor del ciclo celular activo en las células p53-inactivas
Robert S Coleman1, Matthew C Walczak, Erica L Campbell
1Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210-1185, USA. coleman@chemistry.ohio-state.edu
Journal of the American Chemical Society
|November 17, 2005
Resumen
Los investigadores sintetizaron el agente antitumoral lucilactaeno utilizando un nuevo hetero-bis-metalizado 1,3-butadieno. Esta eficiente síntesis total de ocho pasos utilizó acoplamientos secuenciales Stille y Suzuki-Miyaura para el ensamblaje de fragmentos.
Área de la Ciencia:
- Síntesis orgánica La síntesis orgánica.
- Química Medicinal La Química Medicinal es un campo de estudio de la química medicinal.
- Química organometálica Química orgánica de los metales.
Sus antecedentes:
- El lucilactaeno es un agente antitumoral prometedor.
- La síntesis eficiente de productos naturales complejos de polieno sigue siendo un desafío.
Objetivo del estudio:
- Desarrollar una síntesis total eficiente de lucilactaeno.
- Para utilizar el 1,3-butadieno hetero-bis-metalizado en una estrategia de acoplamiento clave.
Principales métodos:
- Empleó el 1,3-butadieno hetero-bis-metalado como un socio de acoplamiento clave.
- Utilizó reacciones secuenciales de acoplamiento cruzado Stille y Suzuki-Miyaura.
- Montó la cadena lateral de pentaeno de lucilactaeno.
Principales resultados:
- Se logró la síntesis total de lucilactaeno.
- La síntesis se completó en sólo ocho pasos lineales.
- Demostró la utilidad de los dienes de boro / estaño en la síntesis de moléculas complejas.
Conclusiones:
- La ruta sintética desarrollada es altamente eficiente.
- Los dienos hetero-bis-metalizados son valiosos sintones para la construcción de sistemas de polieno.
- Esta metodología facilita el acceso a agentes anticancerígenos potenciales.
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