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Una síntesis total concisa de las dictodendrinas F, H e I utilizando éteres de ynol de arilo como bloques de

Wenhan Zhang¹, Joseph M Ready¹

¹Department of Biochemistry, University of Texas Southwestern Medical Center , 5323 Harry Hines Boulevard, Dallas, Texas 75390, United States.

Journal of the American Chemical Society

|July 30, 2016

Resumen

Los investigadores lograron una rápida síntesis total de las dictyodendrinas F, H e I en seis pasos. Este avance utilizó éteres de aril-inol y una nueva cicloadición para construir el complejo núcleo de dictyodendrina de manera eficiente.

Área de la Ciencia:

Química orgánica
Química sintética
Síntesis de productos naturales

Sus antecedentes:

Las dictodendrinas son productos naturales con actividades biológicas potenciales.
Las síntesis anteriores de dictyodendrinas fueron largas y complejas.
Las rutas sintéticas eficientes son cruciales para un mayor estudio y desarrollo analógico.

Objetivo del estudio:

Desarrollar una síntesis total concisa y eficiente de la dictyodendrina F.
Para lograr la primera síntesis total de las dictyodendrinas H e I.
Establecer una nueva estrategia sintética para construir el núcleo de la dictyodendrina.

Principales métodos:

Utilizó éteres de aril-inol como bloques de construcción clave.
Se empleó una nueva reacción de hetero- [2 + 2]-cicloadición entre éteres de ynol de arilo.
Se ejecutó una reacción en cascada retro-4π/6π-electrociclado-N-acylación para formar el núcleo de carbazol.
Se realizó un acoplamiento oxidativo intramolecular consecutivo y una desprotección.

Principales resultados:

Se ha logrado una síntesis total de dictyodendrina F en seis pasos.
Completó la primera síntesis total de las dictyodendrinas H e I.
Construido con éxito el núcleo de dictyodendrina carbazol altamente sustituido.
Demostró la utilidad de los éteres de aril-inol en la síntesis de productos naturales.

Conclusiones:

La vía sintética desarrollada es altamente eficiente y concisa.
Esta metodología proporciona un acceso rápido a las dictyodendrinas F, H e I.
Las nuevas reacciones de cicloadición y cascada representan avances significativos en la química orgánica sintética.

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