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Síntesis total biomimética de (±) -Griffipavixantón a través de una cascada de cicloadición y ciclización catiónica

Kyle D Reichl¹, Michael J Smith¹, Min K Song²

¹Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.

Journal of the American Chemical Society

|September 26, 2017

Resumen

Los investigadores lograron una síntesis concisa del producto natural griffipavixantón. Este enfoque biomimético utilizó una nueva reacción de Diels-Alder para crear la estructura dimérica a partir de una sola molécula precursora.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales
Química biomimética

Sus antecedentes:

Los productos naturales diméricos presentan desafíos sintéticos únicos.
El Griffipavixantón es un producto natural dimérico complejo con un potencial significado biológico.
Las estrategias biomiméticas ofrecen rutas eficientes para moléculas complejas.

Objetivo del estudio:

Desarrollar una síntesis total concisa y biomimética del griffipavixantón.
Explorar una nueva cascada de cicloadición-ciclización intermolecular para el ensamblaje de productos naturales.

Principales métodos:

Utilizó un monómero de xantón prenilado fácilmente accesible como material de partida.
Se empleó una reacción en cascada de cicloadición-ciclización intermolecular [4 + 2].
Promovió la reacción en cascada clave utilizando ácidos de Lewis o Brønsted.
Se realizaron estudios experimentales y computacionales para dilucidar el mecanismo de reacción.

Principales resultados:

Se ha sintetizado con éxito el producto natural dimérico griffipavixantón.
Desarrolló una nueva cascada de cicloadición-ciclización de vinilo p-quinona y dieno.
Se identificó la vía de reacción como una cicloadición catiónica de Diels-Alder por etapas.

Conclusiones:

La síntesis reportada proporciona una ruta eficiente hacia el griffipavixantón.
La nueva reacción en cascada es una herramienta poderosa para construir productos naturales diméricos.
Los estudios mecánicos ofrecen información sobre el control estereocímico de las reacciones de Diels-Alder.

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