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Síntesis total y asignación estereoquímica absoluta de (-) -communesin F
Zhiwei Zuo1, Weiqing Xie, Dawei Ma
1State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Journal of the American Chemical Society
|September 4, 2010
Resumen
Este estudio presenta una síntesis total concisa de (-) -communesin F, detallando una nueva construcción de indolina fusionada con espiro. La investigación también asignó con éxito la configuración absoluta del producto natural.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química sintética de la química sintética.
- Síntesis de Productos Naturales.
Sus antecedentes:
- (-) -Communesin F es un producto natural complejo con un único núcleo de indolina espiro-fundido.
- El establecimiento de rutas sintéticas eficientes y la determinación de configuraciones absolutas son cruciales para comprender la bioactividad de los productos naturales.
Objetivo del estudio:
- Para lograr una síntesis total asimétrica concisa de (-) -communesin F.
- Desarrollar y mostrar una estrategia de acoplamiento oxidativo intramolecular sin precedentes para indolinas fusionadas con espiro.
- Para asignar la configuración absoluta de las comunas naturales (-) en F.
Principales métodos:
- Síntesis total asimétrica utilizando (S) -fenilglicinol protegido por TBS como un auxiliar quiral.
- Formación de anillos G mediada por el mesilato.
- Introducción tardía del anillo A a través de una reacción de Staudinger intramolecular.
- Nuevo acoplamiento oxidativo intramolecular para la elaboración de indolina fusionada con espiro.
Principales resultados:
- Una síntesis de 19 pasos de (-) -communesin F con un rendimiento total de aproximadamente el 6%.
- Aplicación exitosa de una estrategia de acoplamiento oxidativo intramolecular sin precedentes.
- Demostración de una mayor reactividad de las amidas retorcidas en la reacción intramolecular de Staudinger.
- Asignación de la configuración absoluta de las comunas naturales en F como 6R,7R,8R,9S,11R.
Conclusiones:
- La ruta sintética desarrollada es concisa y eficiente para acceder a las comunas (-) en F.
- La nueva estrategia de acoplamiento oxidativo es efectiva para construir la fracción de indolina fusionada con espiro.
- El estudio proporciona información valiosa sobre la reactividad de las amidas retorcidas y confirma la configuración absoluta de las comunidades en F.
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