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Síntesis total asimétrica de (-) -amphidinolide V a través de combinaciones efectivas de transformaciones catalíticas
1Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, Illinois 60607, USA.
Journal of the American Chemical Society
|March 22, 2013
Resumen
Este estudio presenta la primera síntesis total asimétrica de (-) -amphidinolide V, un producto natural complejo. Las reacciones catalizadas por metales clave permitieron la construcción eficiente de su intrincada arquitectura molecular.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química sintética de la química sintética.
- Síntesis de Productos Naturales.
Sus antecedentes:
- (-) -Amphidinolide V es un producto natural marino complejo con actividades biológicas potenciales.
- Las rutas sintéticas eficientes y estereoselectivas son cruciales para acceder a dichas moléculas para su posterior estudio.
Objetivo del estudio:
- Para lograr la primera síntesis total asimétrica de (-) -amphidinolide V.
- Desarrollar y aplicar nuevas metodologías sintéticas para la construcción de moléculas complejas.
Principales métodos:
- Una alcoolisis de silano alquínico catalizado por una base seguida de una metátesis enina de cierre de anillo (RCM) para la formación de 1,3-dieno.
- RCM de dieno y una transposición alilica contractiva en anillo de éteres silílicos cíclicos para la instalación estereoselectiva de una subunidad de 1,5-dieno.
- Condensación directa cruzada de aldol mediada por prolina para la construcción de un intermediario clave de epoxialdehído α,β insaturado.
Principales resultados:
- Finalización con éxito de la síntesis total asimétrica de (-) -amphidinolide V.
- Demostración de transformaciones eficientes catalizadas por metales, incluyendo RCM y condensación de aldol, en una síntesis compleja.
- Construcción estereoselectiva de los principales motivos de dieno y un precursor de epoxialdehído.
Conclusiones:
- La estrategia sintética desarrollada proporciona una ruta viable hacia el (-) -amphidinolide V.
- Esta síntesis pone de relieve el poder de las reacciones catalizadas por metales para hacer frente a objetivos moleculares difíciles.
- Las metodologías empleadas pueden ser aplicables a la síntesis de otros productos naturales complejos.
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