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Síntesis estereodivergente de perhidrobenzos y terpenoides de indeno

Cheng Yang^1,2, Christopher J Huck², Yaroslav D Boyko²

¹Department of Chemistry, Rice University, Houston, Texas 77005, United States.

Journal of the American Chemical Society

|July 7, 2025

Resumen

Este estudio introduce un reordenamiento Rautenstrauch estereodivergente, que permite el acceso a todos los estereoisómeros de núcleos terpenoides de perhidrobenz[e]indeno utilizando catalizadores de oro o paladio. Este método facilita la síntesis total de productos naturales complejos.

Área de la Ciencia:

Química orgánica
Química sintética

Sus antecedentes:

La síntesis estereodivergente ofrece rutas eficientes para moléculas complejas.
Los terpenoides de perhidrobenz[e]indeno representan una clase única de productos naturales con actividades biológicas potenciales.

Objetivo del estudio:

Desarrollar un reordenamiento Rautenstrauch estereodivergente para acceder a los andamios terpenoides de perhidrobenz[e]indeno.
Lograr la síntesis total de productos naturales específicos dentro de esta clase.

Principales métodos:

Se utilizó un reordenamiento estereodivergente de Rautenstrauch con catalizadores de oro (Au) o de paladio (Pd).
Se emplearon estudios computacionales para racionalizar la diastereoselectividad en los pasos de ciclización.
Síntesis totales ejecutadas de la N-acetilpoliveolina, la dasicyfina B y la rabdastina B.

Principales resultados:

Se estableció una entrada sintética uniforme para los cuatro posibles estereoisómeros del núcleo tricíclico 6/6/5.
El análisis computacional explicó con éxito la diastereoselectividad observada durante las reacciones clave de ciclización.
La estrategia permitió la síntesis total exitosa de tres productos naturales distintos.

Conclusiones:

El reordenamiento Rautenstrauch estereodivergente desarrollado proporciona una plataforma versátil para sintetizar terpenos de perhidrobenz[e]indeno.
Esta metodología simplifica el acceso a una amplia gama de productos naturales, mostrando su potencial en síntesis total.
La combinación de desarrollo sintético y conocimientos computacionales ofrece un enfoque poderoso para la síntesis de moléculas complejas.

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