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Síntesis eficientes enantioselectivas de (+) -dalesconol A y B

Guoqing Zhao¹, Guangqing Xu¹, Chao Qian¹

¹State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Ling Ling Road, Shanghai 200032, China.

Journal of the American Chemical Society

|February 23, 2017

Resumen

Este estudio presenta la primera síntesis enantioselectiva de los inmunosupresores (+) -dalesconol A y B. El método eficiente utiliza la catálisis del paladio y una nueva secuencia en cascada para crear moléculas quirales complejas.

Área de la Ciencia:

Química orgánica
Química medicinal
Química sintética

Sus antecedentes:

Los inmunosupresores son cruciales para el trasplante de órganos y el tratamiento de enfermedades autoinmunes.
El Dalesconol A y B son productos naturales complejos con aplicaciones terapéuticas potenciales.
Se necesitan rutas sintéticas eficientes para acceder a estos compuestos para su posterior estudio.

Objetivo del estudio:

Para lograr la primera síntesis enantioselectiva de (+) -dalesconol A y B.
Desarrollar una estrategia sintética muy eficiente y concisa.
Establecer un método robusto para la construcción de la estructura del núcleo de los dalesconols.

Principales métodos:

Cascada de resolución cinética de ciclización dearomativa catalizada por el paladio.
Acoplamiento de Stille esterilizado para la formación de enlaces C-C.
Oxidación de 2,3-dicloro-5,6-diciano-1,4-benzoquinona (DDQ) para introducir la insaturación.
Secuencia de cierre del anillo de hidrólisis en tándem para la formación del producto final.

Principales resultados:

Síntesis enantioselectiva exitosa de (+) -dalesconol A y B.
Alta eficiencia y concisión demostrada en la vía sintética.
Establecimiento de un centro cuaternario quiral de carbono.
Demostración de las reacciones clave, incluido el acoplamiento de Stille y la oxidación de DDQ.

Conclusiones:

La estrategia sintética desarrollada es eficaz para acceder a los dalesconols enantioméricamente puros.
Este trabajo proporciona una plataforma valiosa para la síntesis de compuestos inmunosupresores relacionados.
La metodología destaca los avances en la catálisis asimétrica y la síntesis de moléculas complejas.

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