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Extensión de la química de la reacción del pummerer. Aplicación a la síntesis total de la (+/-) -dibromoagelaspongina

Ken S Feldman¹, Matthew D Fodor

¹Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu

Journal of the American Chemical Society

|October 22, 2008

Resumen

Los investigadores sintetizaron la dibromoagelaspongina, un metabolito de la esponja, utilizando una ruta de 16 pasos desde el imidazol. La síntesis logró el control regioquímico a través de dos ciclizaciones oxidativas, formando el núcleo de triaminometano a través de reacciones tipo Pummerer.

Área de la Ciencia:

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

Sus antecedentes:

Los productos naturales marinos, como los metabolitos de las esponjas, son una rica fuente de nuevas estructuras químicas.
La dibromoagelaspongina es un metabolito de esponja único con una estructura compleja.

Objetivo del estudio:

Desarrollar una vía sintética para el metabolito de la esponja dibromoagelaspongin.
Para investigar la formación del núcleo de triaminometano.

Principales métodos:

Síntesis orgánica en varias etapas a partir del imidazol.
Utilizó dos ciclizaciones oxidativas sucesivas para la formación del núcleo.
Reacciones similares a las de Pummerer empleadas para los precursores del imidazol-2-sulfóxido.

Principales resultados:

Síntesis exitosa de la dibromoagelaspongina en 16 pasos.
Logró un control completo de la regioquímica durante las ciclizaciones oxidativas.
Estableció la formación del inusual núcleo de triaminometano.

Conclusiones:

La ruta sintética desarrollada proporciona acceso a la dibromoagelaspongina.
El estudio aclara el mecanismo de formación del núcleo de triaminometano a través de ciclizaciones oxidativas.

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