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Síntesis total asimétrica catalítica del ácido (-) actinófilo

Lingchao Cai¹, Kui Zhang¹, Ohyun Kwon¹

¹Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.

Journal of the American Chemical Society

|February 25, 2016

Resumen

Este estudio presenta una nueva síntesis asimétrica catalítica del ácido (-) actinófilo. Una anulación quiral clave catalizada por la fosfina crea eficientemente un intermediario de pirrolina, allanando el camino para el ensamblaje de moléculas complejas.

Área de la Ciencia:

Química orgánica
Química sintética
Síntesis asimétrica

Sus antecedentes:

El ácido (-) - Actinofílico es un producto natural complejo con una arquitectura molecular compleja.
Las rutas sintéticas eficientes y estereoselectivas son cruciales para acceder a dichas moléculas para su posterior estudio.

Objetivo del estudio:

Desarrollar una síntesis total asimétrica catalítica del ácido (-) actinófilo.
Establecer nuevas metodologías sintéticas para la construcción de marcos policíclicos complejos.

Principales métodos:

Anulación [3 + 2] quiral catalizada por la fosfina de las iminas y los alenoatos.
Reacciones de acoplamiento catalizadas por cobre.
Acoplamiento de pinacol mediado por yoduro de samario (II).
Deshidroxilación regioselectiva.

Principales resultados:

La síntesis logró un alto rendimiento (99%) y una enantioselectividad (94% ee) en la etapa clave de anulación.
La construcción del anillo de tetrahidroazocina y el ensamblaje del esqueleto complejo fueron exitosos.
Se empleó una deshidroxilación regioselectiva sin precedentes.

Conclusiones:

Se ha establecido una síntesis total asimétrica catalítica robusta y eficiente de ácido (-) actinófilo.
La metodología desarrollada ofrece nuevas estrategias para construir andamios complejos de productos naturales.
Este trabajo amplía el conjunto de herramientas para la síntesis asimétrica en química orgánica.

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