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Ingreso divergente a los alcaloides del tipo gelsedina: Síntesis totales de (-) - gelsedilam, (-) - gelsenicina, (-)

Pingluan Wang¹, Yang Gao¹, Dawei Ma¹

¹State Key Laboratory of Bioorganic & Natural Products Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , China.

Journal of the American Chemical Society

|August 31, 2018

Resumen

Los investigadores desarrollaron una nueva estrategia sintética para los alcaloides de tipo gelsedina, con un núcleo común y diversas estructuras. Este método permitió la rápida síntesis total de cuatro compuestos alcaloides clave.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales
Química medicinal

Sus antecedentes:

Los alcaloides de tipo gelsedina son una clase de productos naturales caracterizados por un núcleo único de oxabiciclo[3.2.2]nonano y una porción de espiro-N-metoxindolinona.
Estos alcaloides poseen un marco compacto con un heterociclo diversamente funcionalizado, que presenta desafíos sintéticos.

Objetivo del estudio:

Desarrollar una estrategia sintética nueva y divergente para acceder a los alcaloides de tipo gelsedina.
Demostrar la eficacia de esta estrategia mediante la síntesis total de cuatro alcaloides específicos del tipo de la gelsedina.

Principales métodos:

La estrategia implica el ensamblaje rápido del núcleo común de oxabiciclo[3.2.2]nonano utilizando una adición asimétrica de Michael.
Un ciclo de oxidación / aldol en tándem y un reordenamiento de pinacol son pasos clave en la construcción del núcleo.
La diversidad estructural se logra a través de la heterociclado en etapa tardía.

Principales resultados:

Se estableció con éxito una vía sintética divergente a los alcaloides de tipo gelsedina.
La estrategia facilitó las síntesis totales muy cortas de gelsedilam, gelsenicina, gelsedina y gelsemoxonina.
El método permite una construcción eficiente de la estructura central y la posterior diversificación.

Conclusiones:

La estrategia sintética presentada ofrece un enfoque potente y eficiente para los alcaloides de tipo gelsedina.
Este trabajo proporciona acceso a productos naturales complejos y puede ayudar en el descubrimiento de nuevos compuestos bioactivos.
La metodología destaca la utilidad de las reacciones asimétricas orquestadas y la funcionalización en etapa tardía.

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