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Montaje rápido de los furanos tetrasubstituidos mediante el reordenamiento de tipo Pummerer

Franz-Lucas Haut, Christoph Habiger, Lukas A Wein

Journal of the American Chemical Society

|January 5, 2021

Resumen

Un nuevo método sintetiza rápidamente furanos altamente sustituidos utilizando una ciclización oxidativa leve de dihidrotiofenos. Este versátil protocolo de síntesis de furanos ofrece altos rendimientos y permite la construcción de moléculas complejas.

Área de la Ciencia:

Química orgánica
Química Heterocíclica

Sus antecedentes:

Existen métodos limitados para la síntesis personalizada de furanos completamente sustituidos.
El desarrollo de protocolos eficientes para los furanos tetrasubstituidos es crucial para la síntesis orgánica.

Objetivo del estudio:

Para informar de un nuevo protocolo rápido para la construcción de tetrasubstituidos, funcional ortogonalmente furans.
Demostrar la versatilidad de los furanos sintetizados como intermediarios en otras transformaciones químicas.

Principales métodos:

Apertura de anillo regioselectivo de los 2,5-dihidrotiofenos.
Ciclización oxidativa con N-clorosuccinimida (NCS) bajo condiciones suaves.
Estudios mecánicos, incluido el análisis computacional, para elucidar las vías de reacción.

Principales resultados:

Se obtienen altos rendimientos de furanos tetrasubstituidos en 30 minutos a temperatura ambiente.
Utilidad demostrada de los furanos en varias reacciones postmodificación.
Reorganización sin precedentes del tipo Pummerer identificada en el mecanismo de reacción.

Conclusiones:

El método desarrollado proporciona una vía potente y eficiente para obtener derivados complejos de furanos.
Los furanos sintetizados son bloques de construcción versátiles para la síntesis orgánica avanzada.
El protocolo fue validado a través de la síntesis total de las pleurotinas A, B y D.

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