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Metatesis cruzada catalítica Z-selectiva en la síntesis de moléculas complejas: una vía estereoselectiva convergente

Alexander W H Speed¹, Tyler J Mann, Robert V O'Brien

¹Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467, United States.

Journal of the American Chemical Society

|November 8, 2014

Resumen

Los investigadores informan de una nueva síntesis de disorazol C1, un compuesto anticancerígeno y antifúngico. Este método utiliza la metatesis cruzada catalítica Z-selectiva para construir de manera eficiente la compleja estructura macrocíclica.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química Medicinal La Química Medicinal es un campo de estudio de la química medicinal.
Síntesis de Productos Naturales.

Sus antecedentes:

El disorazol C1 es un producto natural macrocíclico con importantes actividades anticancerígenas y antifúngicas.
La síntesis eficiente y estereoselectiva de productos naturales complejos es crucial para el descubrimiento y desarrollo de fármacos.

Objetivo del estudio:

Desarrollar una síntesis total convergente, diastereoselectiva y enantioselectiva del disorazol C1.1.
Mostrar la utilidad de la metatesis cruzada catalítica Z-selectiva (CM) en la construcción de macrociclos complejos.

Principales métodos:

Aplicación de la metatesis cruzada catalítica Z-selectiva (CM) para la síntesis estereoselectiva de los ésteres de boronato de Z-alquenilo (B(pin)) y los yoduros de Z-alquenilo.
Una reacción de acoplamiento cruzado inter- e intramolecular catalítica de un solo paso para formar el macrociclo de 30 miembros.

Principales resultados:

Síntesis confiable y eficiente de complejos intermedios Z-alkenil-B (pin) y Z-alkenil yoduro con alta estereoselectividad.
Construcción exitosa del macrociclo de 30 miembros del disorazol C1, con las fracciones críticas de (Z,Z,E) -trieno.

Conclusiones:

La ruta sintética reportada proporciona un método robusto y eficiente para acceder al disorazol C1.
El CM catalítico Z-selectivo es una poderosa herramienta para la síntesis estereocontrolada de macrociclos complejos que contienen polieno.

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