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Síntesis total de epoxiyeujindole A

Zhaohong Lu¹, Hailong Li¹, Ming Bian¹

¹State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

Journal of the American Chemical Society

|September 24, 2015

Resumen

La primera síntesis total de epoxiyeujindole A, un diterpenoide indol único, se logró utilizando un nuevo ciclo catiónico en etapa tardía. Este avance permite un mayor estudio de este complejo producto natural.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales
Química medicinal

Sus antecedentes:

El epoxiyeujindole A es un indol diterpenoide complejo aislado de Eupenicillium javanicum.
Su estructura única presenta un desafío significativo para la síntesis total.

Objetivo del estudio:

Para lograr la primera síntesis total de epoxiyeujindole A.
Desarrollar y mostrar nuevas estrategias sintéticas para productos naturales complejos.

Principales métodos:

La síntesis empleó una estrategia de ciclización catiónica en etapa tardía.
Los pasos clave incluyeron adición / alquilación conjugada enantioselectiva, ciclización de Luche, reacción Nozaki-Hiyama-Kishi, acoplamiento Suzuki-Miyaura y reacción de Prins.

Principales resultados:

Construcción exitosa del sistema de anillos del CDE.
Montaje eficiente del anillo A fuertemente sustituido.
Formación del anillo B fusionado puente.
Finalización de la síntesis total del epoxiyeujindole A.

Conclusiones:

Se ha logrado con éxito la síntesis total de epoxiyeujindole A.
La vía sintética desarrollada proporciona una plataforma valiosa para explorar las actividades biológicas del epoxiyeujindole A y sus análogos.

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