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Síntesis total de las rodomolinas A y B

Weizhao Zhao¹, Duo Zhang¹, Yuran Wang¹

¹State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, Gansu Province 730000, China.

Journal of the American Chemical Society

|November 28, 2023

Resumen

Los investigadores lograron las primeras síntesis totales asimétricas de rodomolinas A y B, grayanoides complejos. Esto implicó una estrategia convergente, ensamblando fragmentos clave y construyendo el núcleo único de oxa-biciclo [3.2.1].

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales

Sus antecedentes:

Las rodomolinas A y B son grayanoides de tipo rodomolano.
Estos productos naturales poseen un esqueleto de carbono d-homograyanano único y un núcleo oxa-biciclo [3.2.1].

Objetivo del estudio:

Para lograr las primeras síntesis totales asimétricas de rodomolinas A y B.
Desarrollar una estrategia convergente para la construcción de estructuras grisáceas complejas.

Principales métodos:

Estrategia de síntesis convergente
Acoplamiento silencioso y intercambio de litio-halógeno para el ensamblaje de fragmentos.
S_N2 sustitución intramolecular de sulfato cíclico para la formación de núcleos de oxa-biciclo[3.2.1].
Reorganización de Payne y Meinwald y transformaciones redox para la funcionalización del anillo A.

Principales resultados:

Síntesis total exitosa y asimétrica de las rodomolinas A y B.
Construcción eficiente del esqueleto d-homograyanano y el núcleo oxa-biciclo [3.2.1].
Control estereoselectivo durante toda la vía sintética.

Conclusiones:

La estrategia convergente desarrollada es eficaz para sintetizar grayanoides complejos.
Este trabajo proporciona acceso a las rodomolinas A y B para futuras investigaciones biológicas.
La metodología sintética puede aplicarse a otros productos naturales complejos.

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