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Síntesis total enantioselectiva de (-) - Pavidolida B

Peng-Peng Zhang¹, Zhi-Ming Yan¹, Yuan-He Li²

¹Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen 518055, China.

Journal of the American Chemical Society

|September 6, 2017

Resumen

La síntesis enantioselectiva de (-) - pavidolida B se logró en 10 pasos. Los métodos clave incluyeron la ciclopropanación organocatalítica y la anulación en cascada de radicales para una lactona compleja.

Área de la Ciencia:

Química orgánica
Química sintética

Sus antecedentes:

(-) Pavidolida B es un producto natural complejo con una estructura tricíclica única.
Las rutas sintéticas eficientes son cruciales para acceder y estudiar tales moléculas.

Objetivo del estudio:

Desarrollar una síntesis concisa y enantioselectiva de (-) pavidolida B.
Establecer metodologías clave para la construcción de lactonas altamente funcionales con múltiples estereocentros.

Principales métodos:

Se empleó una síntesis lineal de 10 pasos.
La transformación clave fue la organocatalítica enantioselectiva.
Se utilizó una estrategia de anulación en cascada basada en radicales para la construcción del núcleo.

Principales resultados:

La síntesis dio con éxito (-) - pavidolida B.
El paso clave de anulación estableció siete estereocentros contiguos con alta regio- y diastereoselectividad.
El núcleo tricíclico de la molécula objetivo fue ensamblado eficientemente.

Conclusiones:

Se ha establecido una vía práctica y enantioselectiva para el (-) - pavidolida B.
Los métodos sintéticos desarrollados son aplicables a otros productos naturales complejos de lactona.
Este trabajo muestra el poder de la organocatálisis y la química radical en la síntesis de moléculas complejas.

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