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Síntesis total, revisión de la estructura y configuración absoluta del (-) -brevenal
Haruhiko Fuwa1, Makoto Ebine, Andrea J Bourdelais
1Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Aoba-ku, Sendai 981-8555, Japan.
Journal of the American Chemical Society
|December 21, 2006
Resumen
Los investigadores lograron la síntesis total de brevenal, un producto natural de poliéter marino. El análisis estructural reveló que el producto natural es probablemente un epímero de la estructura inicialmente propuesta, ahora confirmada por síntesis.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Síntesis de Productos Naturales.
- Productos Naturales Marinos Productos Naturales Marinos
Sus antecedentes:
- Brevenal es un éter policíclico no tóxico producto natural aislado de Karenia brevis.
- La estructura inicialmente propuesta del brevenal carecía de una asignación estereocímica definitiva.
Objetivo del estudio:
- Para lograr la síntesis total de la estructura propuesta de brevenal.
- Revisar y confirmar la estructura del brevenal basado en datos y síntesis espectroscópicas.
- Para establecer la configuración absoluta del producto natural.
Principales métodos:
- El ensamblaje convergente del esqueleto de poliéter pentacíclico utilizando el acoplamiento Suzuki-Miyaura.
- Construcción estereoselectiva de la cadena lateral de dienal a través del acoplamiento modificado de Stille promovido por tiofen-2-carboxilato (CuTC) de cobre.
- Comparación espectroscópica RMN detallada entre los compuestos sintéticos y el producto natural.
Principales resultados:
- Se logró la síntesis total de la estructura inicialmente propuesta (1).
- Las discrepancias en los espectros de RMN indicaron que era necesaria una revisión estructural.
- El producto natural fue identificado como el epímero C26 (2) de la estructura propuesta.
- La estructura revisada (2) fue validada a través de su síntesis total, confirmando la configuración absoluta.
Conclusiones:
- La síntesis total de brevenal y su epímero proporciona una asignación estructural y estereoquímica definitiva.
- Este trabajo revisa la estructura conocida del brevenal, un importante poliéter marino.
- Las estrategias sintéticas desarrolladas son aplicables a otros productos naturales complejos de éter policíclico.
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