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Síntesis total de aflavazol y 14-hidroxiaflavina

Hailong Li¹, Qifeng Chen¹, Zhaohong Lu¹

¹State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

Journal of the American Chemical Society

|December 10, 2016

Resumen

Los investigadores lograron las primeras síntesis totales de aflavazol y 14-hidroxiaflavina, los diterpenoides complejos del indole. Las etapas clave incluyeron la ciclización de Prins promovida por AlI3 y reacciones de acoplamiento avanzadas para el ensamblaje estructural.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales
Química medicinal

Sus antecedentes:

Los diterpenoides indoles son una clase de productos naturales complejos con actividades biológicas significativas.
El aflavazol y la 14-hidroxiaflavinina son miembros estéricamente exigentes de esta clase, lo que plantea desafíos sintéticos.
Los esfuerzos sintéticos anteriores no han logrado la síntesis total de estos compuestos específicos.

Objetivo del estudio:

Para lograr las primeras síntesis totales de aflavazol y 14-hidroxiaflavina.
Desarrollar nuevas estrategias sintéticas para la construcción de indol diterpenoides estérilmente obstaculizados.
Explorar la utilidad de las reacciones específicas en el ensamblaje de arquitecturas moleculares complejas.

Principales métodos:

Ciclización de Prins promovida por el ioduro de aluminio (AlI3) para la formación de la estructura del núcleo.
Se empleó una secuencia de electrociclado-aromatización para construir la fracción de areno pentasubstituido.
Se aplica el acoplamiento Stille-Migita para ensamblar la olefina tetrasubstituida.
Incorporación de la escisión reductiva en etapa tardía de los enlaces bencílicos y alilicos C-O.

Principales resultados:

Se sintetizó con éxito el aflavazol (6) y la 14-hidroxiaflavinina (8).
Demostró la eficacia de la ciclización de AlI3-promovida por el alquino Prins en la construcción de motivos complejos.
Se han establecido rutas eficientes para el ensamblaje de sistemas aromáticos y olefínicos altamente sustituidos.
Se han logrado manipulaciones de grupos funcionales en fase avanzada para obtener los productos naturales objetivo.

Conclusiones:

Se realizaron con éxito las primeras síntesis totales de aflavazol y 14-hidroxiaflavina.
Las estrategias sintéticas desarrolladas proporcionan una plataforma robusta para acceder a los diterpenoides de indol complejos.
Este trabajo amplía el conjunto de herramientas sintéticas para la construcción de productos naturales estériles congestionados.

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