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Síntesis total de (+) pleuromutilina
Elliot P Farney1, Sean S Feng1, Felix Schäfers1
1The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
Journal of the American Chemical Society
|January 12, 2018
Resumen
Se desarrolló una síntesis de 18 pasos del antibiótico (+) -pleuromutilina utilizando reacciones estereoselectivas clave. Este avance permite la creación de nuevos antibióticos mutilinos para futuras aplicaciones terapéuticas.
Área de la Ciencia:
- Síntesis orgánica
- Química medicinal
- Desarrollo de antibióticos
Sus antecedentes:
- La pleuromutilina es un antibiótico natural con un núcleo de diterpenos tetraciclicos único.
- Las rutas sintéticas existentes para la pleuromutilina a menudo son largas y complejas.
- El desarrollo de estrategias sintéticas eficientes es crucial para acceder a nuevos análogos.
Objetivo del estudio:
- Para revelar una nueva y eficiente síntesis de 18 pasos del antibiótico (+) -pleuromutilina.
- Establecer centros estereoscópicos clave utilizando metodologías sintéticas avanzadas.
- Proporcionar una plataforma para la síntesis de nuevos antibióticos basados en mutilinas.
Principales métodos:
- Empleó una secuencia sintética de 18 pasos.
- Se utilizó la ciclización mediada por samario (SmI2) para construir el anillo de ocho miembros.
- Implementó una transferencia estereospecífica de átomo de hidrógeno transanular [1,5] para controlar la estereocímica del C10.
Principales resultados:
- Se ha sintetizado con éxito (+) -pleuromutilina en 18 pasos.
- Se ha logrado una alta estereoselectividad en la etapa de ciclización mediada por SmI2.
- Se ha demostrado la capacidad de preparar (+) -12-epi-pleuromutilina utilizando la misma estrategia.
Conclusiones:
- La vía sintética desarrollada es eficiente y está controlada por estéreo.
- Las reacciones clave de ciclización y transferencia de hidrógeno son robustas.
- Este enfoque sintético facilita la exploración de nuevos derivados de los antibióticos mutilinos.
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