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Síntesis total de penicibilaenos habilitada por una reacción de tipo doble coniaeno en tándem

Zheyuan Wang¹, Zhilin Song¹, Jun Huang²

¹State Key Laboratory of Chemical Oncogenomics and Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.

Journal of the American Chemical Society

|February 8, 2024

Resumen

Se ha logrado la síntesis total de los penicibilaenos A y B. Una nueva reacción tándem de coniaeno construyó eficientemente el complejo núcleo tricíclico, seguido de pasos estereoselectivos para establecer centros quirales clave.

Área de la Ciencia:

Síntesis orgánica
Química de los productos naturales
Química medicinal

Sus antecedentes:

Los penicibilaenos A y B son productos naturales complejos con actividades biológicas potenciales.
Las rutas sintéticas eficientes son cruciales para una mayor evaluación biológica y el desarrollo analógico.

Objetivo del estudio:

Para lograr la primera síntesis total de los penicibilaenos A y B.
Desarrollar una estrategia sintética novedosa y eficiente para la construcción de la estructura única del núcleo tricíclico.

Principales métodos:

Se empleó una reacción clave en tándem de tipo coniaeno de 5 exo-dig y 6 exo-dig.
La adición conjugada mediada por cobre y la hidrogenación de Crabtree se utilizaron para la síntesis estereoselectiva.

Principales resultados:

El núcleo tricíclico [6.3.1.0^1,5] de dodecano se instaló con éxito en un solo paso a partir de un precursor de dibutinilo ciclohexanona.
Los centros estereogénicos en C5 y C2 fueron forjados con precisión, llevando a las moléculas objetivo.

Conclusiones:

La vía sintética descrita proporciona un acceso eficiente a los penicibilaenos A y B.
La metodología desarrollada, en particular la reacción tándem de conio, ofrece una herramienta poderosa para la construcción de sistemas policíclicos complejos.

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