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Síntesis enantioselectiva del ácido pentacicloanammóxico

Vincent Mascitti¹, E J Corey

¹Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

Journal of the American Chemical Society

|March 9, 2006

Resumen

Los investigadores lograron una síntesis enantioselectiva de ácido pentacicloanammóxico, un ácido graso único de Candidatus Brocadia anammoxidans. Este avance proporciona acceso a ambos enantiómeros para estudios de biosíntesis sin precedentes.

Área de la Ciencia:

Química orgánica es la química orgánica.
Síntesis de Productos Naturales.
La bioquímica es la bioquímica.

Sus antecedentes:

El ácido pentacicloanammóxico (1) es un ácido graso inusual de origen natural identificado en el Candidatus Brocadia anammoxidans.
La biosíntesis de esta estructura C20 única no se entiende bien y parece sin precedentes.
El acceso a cantidades suficientes de ácido pentacicloanamóxico y su enantiómero es crucial para futuras investigaciones.

Objetivo del estudio:

Desarrollar una síntesis enantioselectiva altamente efectiva para el ácido pentacicloanamóxico (1).
Para permitir futuros estudios sobre el modo sin precedentes de biosíntesis de este producto natural.
Hacer que ambos enantiómeros del ácido pentacicloanamóxico estén disponibles para la investigación.

Principales métodos:

Ensamblaje estereocontrolado de la estructura C20 del ácido pentacicloanammósico.
Utilizó cuatro bloques de construcción clave: ciclobuteno, 2-ciclopentenona, silisilciclopentenona quiral 6 y ácido 7-bromoheptanoico.
Estrategia de síntesis enantioselectiva. estrategia de síntesis enantioselectiva.

Principales resultados:

Se logró con éxito una síntesis enantioselectiva altamente efectiva de ácido pentacicloanammóxico (1).
La síntesis permitió el ensamblaje estereocontrolado de la compleja estructura C20.
Tanto el ácido pentacicloanammóxico (1) como su enantiómero están ahora disponibles en cantidades suficientes.

Conclusiones:

La vía sintética desarrollada proporciona un acceso confiable al ácido pentacicloanammóxico y su enantiómero.
La disponibilidad de ambos enantiómeros facilitará la investigación futura en su única vía biosintética.
Este trabajo sienta las bases para la comprensión de una biosíntesis de productos naturales sin precedentes.

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