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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

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Published on: October 4, 2019

Una síntesis en 16 pasos del isoryanodano diterpeno (+) -perseanol

Arthur Han¹, Yujia Tao¹, Sarah E Reisman²

¹Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, USA.

|September 27, 2019

Resumen

Los investigadores sintetizaron el (+) -perseanol, un compuesto insecticida natural, mediante un proceso de 16 pasos. Esta síntesis eficiente de diterpenos complejos ofrece nuevas vías para los agentes de control de plagas.

Área de la Ciencia:

Química de los productos naturales
Síntesis orgánica
Toxicología de los insectos

Sus antecedentes:

El (+) -perseanol es un diterpeno isorianodano de la especie Persea indica con propiedades insecticidas.
Está estructuralmente relacionado con la (+) -rianodina, un modulador de los canales de calcio (receptores de ryanodina).
Los isorianodanos que carecen del grupo éster, como el perseanol, pueden mostrar actividad insecticida selectiva.

Objetivo del estudio:

Para obtener una síntesis química de (+) -perseanol.
Desarrollar una ruta eficiente para diterpenos complejos y altamente oxidados.

Principales métodos:

Una síntesis de 16 pasos a partir de (R) pulegón.
Utilizó una anulación de dos pasos para construir el núcleo tetraciclico.
Se utiliza el acoplamiento de fragmentos convergentes y la oxidación estratégica.

Principales resultados:

Síntesis exitosa del (+) -perseanol.
Demostró una ruta concisa a los diterpenos complejos.
Se estableció un método para ensamblar el núcleo tetraciclico a partir de unidades de ciclopentilo.

Conclusiones:

La síntesis proporciona una vía viable para el (+) -perseanol.
Las estrategias de síntesis convergentes son efectivas para productos naturales complejos.
Este trabajo avanza en la síntesis de diterpenos insecticidas.

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