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Síntesis eficientes de las korupensaminas A, B y la micelamina B mediante reacciones asimétricas de acoplamiento

Guangqing Xu¹, Wenzhen Fu, Guodu Liu

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

Journal of the American Chemical Society

|October 24, 2013

Resumen

Este estudio introduce un eficiente acoplamiento asimétrico Suzuki-Miyaura para la síntesis de productos naturales de biarilo quiral. Estos métodos permiten una síntesis concisa y estereoselectiva de moléculas complejas como la micelamina B.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.
Síntesis de Productos Naturales.

Sus antecedentes:

Los productos naturales de Chiral biaryl poseen estructuras complejas y actividades biológicas significativas.
Las rutas sintéticas eficientes y estereoselectivas son cruciales para acceder a estos valiosos compuestos.

Objetivo del estudio:

Desarrollar por primera vez reacciones de acoplamiento asimétricas Suzuki-Miyaura eficientes en la síntesis total de la korupensamina A y B.
Para lograr una síntesis concisa y estereoselectiva de la micelamina B mediante la combinación de acoplamiento asimétrico Suzuki-Miyaura con hidrogenación diastereoselectiva.

Principales métodos:

Utilizó reacciones asimétricas de acoplamiento Suzuki-Miyaura con nuevos ligandos quirales monofosforados (L1-3).
Se empleó un paso de hidrogenación diastereoselectiva.
Investigó el papel de las interacciones polar-π en el logro de una alta enantioselectividad.

Principales resultados:

Se sintetizó con éxito una serie de biarilos quirales funcionalizados con excelentes rendimientos y altas enantioselectividades (hasta el 99% ee).
Demostró la primera aplicación del acoplamiento asimétrico Suzuki-Miyaura en la síntesis total de la korupensamina A y B.
Logró una síntesis concisa y estereoselectiva de la micelamina B.

Conclusiones:

Los ligandos monofosforados quirales son altamente efectivos para el acoplamiento asimétrico Suzuki-Miyaura, proporcionando acceso a valiosos biarilos quirales.
La metodología desarrollada ofrece una poderosa estrategia para la síntesis estereoselectiva de productos naturales complejos.
Las interacciones Polar-π se proponen como un factor clave para la alta enantioselectividad observada.

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