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Síntesis total asimétrica de (-) -Communesin F catalizada por IR

Xiao Liang^1,2, Tian-Yuan Zhang^1,2, Xue-Yi Zeng¹

¹State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.

Journal of the American Chemical Society

|February 21, 2017

Resumen

Los investigadores lograron la primera síntesis total asimétrica catalítica del alcaloide heptacíclico (-) -communesin F. Esto implicó una ciclización en cascada catalizada por iridio para construir la estructura del núcleo y una nueva reducción / ciclización para el cierre del anillo final.

Área de la Ciencia:

Química orgánica
Química sintética
Síntesis de productos naturales

Sus antecedentes:

(-) -communesin F es un alcaloide heptacíclico complejo con una estructura única.
Las rutas sintéticas anteriores hacia las comunas F y sus análogos han sido limitadas.
La síntesis asimétrica catalítica ofrece un enfoque eficiente para moléculas complejas.

Objetivo del estudio:

Desarrollar la primera síntesis total asimétrica catalítica de (-) -communesin F.
Establecer una nueva estrategia sintética para construir el complejo núcleo heptacíclico.
Demostrar la utilidad de las reacciones en cascada catalizadas por iridio en la síntesis de productos naturales.

Principales métodos:

Ciclización en cascada intermolecular asimétrica catalizada por iridio para formar el núcleo tetraciclico CDEF.
Reducción de una amida retorcida y ciclización activada por mezilación para el cierre del anillo A.
Construcción estereoselectiva de múltiples centros quirales.

Principales resultados:

Síntesis total exitosa y eficiente de (-) -communesin F.
Establecimiento de una ciclización en cascada catalizada por iridio clave para la construcción rápida del núcleo.
Desarrollo de un nuevo método para la formación de la fase tardía del anillo A.

Conclusiones:

La vía sintética descrita representa un avance significativo en la síntesis total de alcaloides complejos.
La metodología proporciona una poderosa plataforma para acceder a las comunidades F análogas.
Este trabajo destaca el potencial de las reacciones en cascada para agilizar la síntesis de moléculas complejas.

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