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Síntesis rápida de análogos de acilfloroglucinol poliprenilado a través de la anulación alelica conjuntiva

Alexander J Grenning¹, Jonathan H Boyce, John A Porco

¹Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University , 590 Commonwealth Ave., Boston, Massachusetts 02215, United States.

Journal of the American Chemical Society

|July 26, 2014

Resumen

Desarrollamos una nueva síntesis para los poliprenilados complejos de acilfloroglucinol (PPAP). Este método crea rápidamente diversos análogos de PPAP con actividades biológicas potenciales utilizando alilación decarboxilativa doble y alilación alelica conjuntiva dearomativa.

Área de la Ciencia:

Química orgánica es la química orgánica.
Síntesis de Productos Naturales.
Química Medicinal La Química Medicinal es el campo de la Química Medicinal.

Sus antecedentes:

Los acilfloroglucinolos poliprenilados (PPAP) son una clase de productos naturales complejos.
Los PPAP exhiben actividades biológicas significativas y prometedoras.
Los métodos de síntesis existentes para los PPAP pueden ser largos y carecen de diversidad.

Objetivo del estudio:

Desarrollar una síntesis novedosa, eficiente y orientada a la diversidad para los análogos de PPAP.
Establecer una estrategia inspirada en la biosíntesis para acceder a arquitecturas moleculares complejas.
Para permitir una rápida exploración de la relación estructura-actividad de los PPAP.

Principales métodos:

Utilizó una alilación decarboxilativa doble (DcA) de andamios de acilfloroglucinol.
Empleado dearomative conjunctive allylic alkylation (DCAA) para una mayor elaboración estructural.
Desarrolló una estrategia inspirada en las vías de biosíntesis de productos naturales.

Principales resultados:

Se han sintetizado con éxito diversos análogos de los acilfloroglucinolos poliprenilados.
Demostró la utilidad de las reacciones de DcA y DCAA en la síntesis de PPAP.
Generó alil-desoxihumulonas como intermediarios clave.

Conclusiones:

El enfoque de síntesis presentado proporciona un acceso rápido a una amplia gama de análogos de PPAP.
Este método es valioso para descubrir nuevos compuestos bioactivos dentro de la clase de PPAP.
La estrategia ofrece una poderosa herramienta para la exploración de la química medicinal de los PPAP.

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