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Síntesis total del (+) -amphidinolido A. El montaje de los fragmentos
Barry M Trost1, Stephen T Wrobleski, John D Chisholm
1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Journal of the American Chemical Society
|September 30, 2005
Resumen
La síntesis total del anphidinolide A, un macrólido citotóxico, se ha logrado utilizando métodos químicos avanzados. Esta investigación corrige la estructura previamente reportada del anphidinolide A, proporcionando una determinación estructural definitiva.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química Medicinal La Química Medicinal es un campo de estudio de la química medicinal.
- Química de los macrólidos
Sus antecedentes:
- Amphidinolide A es un macrolido citotóxico con una estructura compleja.
- Los esfuerzos sintéticos anteriores indicaron una asignación estructural incorrecta para el anfidinolide A.
- La molécula presenta dos subunidades de 1,4-dieno saltadas.
Objetivo del estudio:
- Para dilucidar y confirmar la estructura correcta del anphidinolide A a través de la síntesis total.
- Desarrollar una estrategia sintética flexible y convergente para macrolides complejos.
- Para proporcionar acceso a múltiples diastereómeros para la asignación estructural definitiva.
Principales métodos:
- Síntesis total del anfidinolido A.
- Acoplamientos alqueno-alquina catalizados por rutenio para la formación de dieno.
- Transformaciones asimétricas catalíticas para el control estereocéntrico.
- Análisis espectroscópico de RMN para elucidación estructural.
Principales resultados:
- Se desarrolló con éxito una ruta sintética altamente convergente.
- Se sintetizaron los principales productos intermedios (5, 6 y 7).
- Se accedió a múltiples diastereómeros del anfidinolide A para la determinación estructural.
- La estructura correcta del anphidinolide A fue establecida definitivamente.
Conclusiones:
- La síntesis total y el análisis espectroscópico determinaron con éxito la estructura correcta del anfidinolide A.
- La metodología sintética desarrollada ofrece flexibilidad para acceder a macrolides complejos.
- Este trabajo corrige las asignaciones erróneas estructurales anteriores y proporciona una base para futuras investigaciones sobre la actividad biológica del anphidinolide A.
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