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Síntesis total del ácido (-) -nodulispórico D

Yike Zou¹, Jason E Melvin¹, Stephen S Gonzales¹

¹Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.

Journal of the American Chemical Society

|June 2, 2015

Resumen

Los investigadores lograron una síntesis total del complejo indole diterpenoide (-) - ácido nodulispórico D. Esto implicó pasos clave como la difuncionalización vicinal y un protocolo de acoplamiento cruzado / indolización en cascada.

Área de la Ciencia:

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

Sus antecedentes:

Los diterpenoides indoles son una clase de productos naturales complejos con actividades biológicas significativas.
El ácido (-) -nodulispórico D es un miembro arquitectónicamente complejo de esta clase, lo que plantea un desafío sintético.

Objetivo del estudio:

Desarrollar una síntesis convergente total de ácido (-) -nodulispórico D.
Establecer rutas sintéticas eficientes para la construcción de estructuras diterpenoides indolas complejas.

Principales métodos:

Estrategia de síntesis total convergente. estrategia de síntesis total convergente.
Difuncionalización vicinal de los aldehídos α,β insaturados.
Reacciones de acoplamiento cruzado en cascada y de indolización.

Principales resultados:

Construcción exitosa del sistema de anillos E,F-transfundido de 5,6.
Formación del núcleo indólico multisubstituido del CDE.
Se logró una síntesis completa de ácido (-) -nodulispórico D.

Conclusiones:

La estrategia sintética desarrollada es efectiva para la síntesis compleja de indol diterpenoide.
Las transformaciones clave permiten un acceso eficiente a la molécula objetivo.
Esta síntesis proporciona una base para una mayor exploración de los derivados del ácido nodulispórico.

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