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Updated: Dec 28, 2025

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

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

Published on: October 4, 2019

Síntesis divergente de los diterpenos antivirales Wickerols A y B

Jiachen Deng¹, Yuhan Ning¹, Hailong Tian¹

¹CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Journal of the American Chemical Society

|February 20, 2020

Resumen

Los investigadores sintetizaron nuevos compuestos antivirales, los wickerols A y B, que presentan una estructura de anillo fusionado única. Este estudio confirma sus configuraciones y demuestra una vía sintética viable para estos potentes inhibidores del virus de la gripe.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales
Química medicinal

Sus antecedentes:

Los wickerols A y B son productos naturales de diterpenos con un marco de anillo 6-5-6-6 fundido único.
Estos compuestos muestran una actividad antiviral significativa contra el virus de la influenza A H1N1.

Objetivo del estudio:

Desarrollar una síntesis divergente para los wickerols A y B.
Para confirmar las configuraciones absolutas de los mimbres A y B.

Principales métodos:

La síntesis se inicia a partir de la sitolactona disponible en el mercado.
Los pasos clave incluyeron la ciclización reductora mediada por SmI2, la reorganización de Claisen y la reacción de alquilación intramolecular / aldol.
Se logró el ensamblaje estereocontrolado del núcleo tetraciclico.

Principales resultados:

Síntesis exitosa de los wickerols A y B en 16 y 15 pasos, respectivamente.
La ruta sintética construyó de manera eficiente el complejo marco tetraciclico.
Se confirmaron las configuraciones absolutas de los wickerols A y B.

Conclusiones:

Se estableció una estrategia sintética práctica y eficiente para los wickerols A y B.
La síntesis proporciona acceso a estos potentes agentes antivirales para su posterior estudio.
Este trabajo valida las asignaciones estructurales y proporciona una base para explorar productos naturales relacionados.

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