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Una reacción intermolecular acelerada de Rauhut-Currier permite la síntesis total de (-) -flueggenina C
Sangbin Jeon1,2, Sunkyu Han1,2
1Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST) , Daejeon 34141, Korea.
Journal of the American Chemical Society
|April 25, 2017
Resumen
Los investigadores lograron la primera síntesis total del alcaloide dimérico (-) -flueggenina C utilizando una reacción intermolecular acelerada de Rauhut-Currier (RC). Este avance permite una síntesis eficiente de productos naturales complejos diméricos.
Área de la Ciencia:
- Química orgánica
- Síntesis de productos naturales
- Química medicinal
Sus antecedentes:
- Los alcaloides de Securinega son una clase de productos naturales con diversas actividades biológicas.
- Los esfuerzos sintéticos anteriores se han centrado en las securinegas monoméricas, y las estructuras diméricas siguen siendo sintéticamente difíciles.
- La reacción enzimática de Rauhut-Currier (RC) es una vía propuesta para la formación de securinegas diméricas, pero no se ha realizado sintéticamente.
Objetivo del estudio:
- Para lograr la primera síntesis total del alcaloide dimérico securinega (-) -flueggenina C.
- Desarrollar una reacción intermolecular Rauhut-Currier (RC) eficiente y diastereoselectiva para la construcción de productos naturales diméricos.
- Explorar la utilidad de un sustrato de enona modificado para acelerar la reacción RC.
Principales métodos:
- Síntesis total de (-) -flueggenina C.
- Desarrollo de una reacción intermolecular acelerada de Rauhut-Currier (RC).
- Instalación estratégica de un grupo funcional nucleófilo en la posición γ de una enona.
- Formación diastereoselectiva de un intermediario dimérico.
Principales resultados:
- Se completó con éxito la primera síntesis total de (-) -flueggenina C.
- Se estableció una reacción intermolecular de Rauhut-Currier (RC) acelerada y diastereoselectiva.
- El intermediario dimérico clave fue sintetizado eficientemente.
- La estrategia sintética resultó eficaz para acceder a alcaloides diméricos complejos.
Conclusiones:
- La metodología sintética desarrollada permite la construcción eficiente de alcaloides de securinega dimérico.
- Este trabajo proporciona una plataforma valiosa para la síntesis de otros productos naturales diméricos complejos.
- La reacción RC intermolecular acelerada es una herramienta poderosa en la química orgánica sintética.
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