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Síntesis total de la (+) -Shearilicina

Daria E Kim¹, Yingchuan Zhu¹, Shingo Harada^1,2

¹Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Journal of the American Chemical Society

|February 15, 2023

Resumen

Los investigadores lograron la primera síntesis total de la shearilicina, un diterpenoide complejo de indol. Este proceso de 11 pasos utilizó un auxiliar quiral y una ciclización intramolecular de Heck para una construcción eficiente de moléculas.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales
Química medicinal

Sus antecedentes:

Los diterpenoides indoles son una clase de productos naturales con estructuras complejas y diversas actividades biológicas.
La shearilicina es un diterpenoide indólico específico cuya síntesis total no se ha informado previamente.
El acceso a los diterpenoides de indol altamente oxidados presenta desafíos sintéticos significativos.

Objetivo del estudio:

Informar sobre la primera síntesis total del producto natural shearilicina.
Desarrollar una vía sintética generalizable aplicable a los diterpenoides de indol altamente oxidados.
Explorar estrategias eficientes para la construcción de la subestructura del núcleo del carbazol.

Principales métodos:

Se diseñó y ejecutó una secuencia sintética de 11 pasos.
Se empleó una estrategia auxiliar quiral nativa para la síntesis enantiospecífica.
Se utilizó una ciclización intramolecular de Heck para la formación de anillos de carbazolos.

Principales resultados:

Se completó con éxito la síntesis total de shearilicina.
Se estableció un precursor generalizable para los diterpenoides indoles altamente oxidados.
Los estudios computacionales aclararon las interacciones no covalentes que facilitan el paso clave de ciclización de Heck.

Conclusiones:

La vía sintética desarrollada proporciona un acceso eficiente a la shearilicina y a los diterpenoides indólicos relacionados.
El uso de un auxiliar quiral asegura la enantioespecificidad en la síntesis.
La ciclización intramolecular de Heck es una transformación clave, optimizada a través de conocimientos computacionales.

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