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Equivalentes de Bisketeno en forma de Diels-Alder Dienes

Isuru Dissanayake¹, Jacob D Hart¹, Emma C Becroft¹

¹Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia.

Journal of the American Chemical Society

|July 21, 2020

Resumen

Los 2,5- ((Bistert-butyldimethylsilyloxy) furanos sirven como dienos versátiles en las reacciones de Diels-Alder, proporcionando una síntesis leve y eficiente de para-hidroquinonas y para-benzoquinonas sustituidas. Este método también produce para-iminoquinonas y permite la síntesis de productos naturales.

Área de la Ciencia:

Química orgánica
Química sintética
Metodología de reacción

Sus antecedentes:

Los 2,5- ((Bistert-butyldimethylsilyloxy) furanos son reconocidos como equivalentes eficaces del bisceteno en las zonas circundantes.
Estos compuestos son dienos valiosos para las reacciones de cicloadición, particularmente la reacción de Diels-Alder.

Objetivo del estudio:

Para explorar la utilidad de 2,5- ((Bistert-butyldimethylsilyloxy) furans como dienes en las reacciones de Diels-Alder.
Desarrollar una síntesis convergente para parahidroquinonas altamente sustituidas y compuestos relacionados.
Demostrar la aplicación de estos derivados de furano en la síntesis de productos naturales.

Principales métodos:

Reacciones de cicloadición de Diels-Alder en las que se utilizan como dienos los 2,5-bis (tert-butildimetilsililoxi) furanos.
Utilizan dienófilos olefinos y acetilenos, incluidas las bencinas.
Una secuencia de una olla que involucra la cicloadición de Diels-Alder, la apertura de anillos y la tautomerización.

Principales resultados:

Síntesis convergente y leve de parahidroquinonas no protegidas y altamente sustituidas.
Síntesis exitosa de parabenzoquinonas utilizando dienófilos acetilénicos.
Establecimiento de 2,5-bis ((tert-butildimethylsilyloxy) pirroles como dienos para la síntesis de para-iminoquinona.
Síntesis en escala de gramos del agente neuroprotector (±) indostatina.

Conclusiones:

Los 2,5- ((Bistert-butyldimethylsilyloxy) furanos son dienos altamente efectivos para las reacciones de Diels-Alder, que ofrecen una ruta leve a valiosos derivados de la quinona.
La metodología desarrollada proporciona un acceso eficiente a estructuras complejas, incluidos los productos naturales.
Este enfoque amplía el alcance de los equivalentes de dieno en la síntesis orgánica.

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