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Síntesis de la (-) -sordarina en su síntesis
Shunsuke Chiba1, Mitsuru Kitamura, Koichi Narasaka
1Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Journal of the American Chemical Society
|May 25, 2006
Resumen
La primera síntesis total de (-) -sordarina se logró utilizando la nueva ciclización de radicales oxidativos catalizados por Ag ((I) y la alilación intramolecular catalizada por Pd ((0). Esta investigación proporciona una nueva ruta sintética para esta compleja molécula.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química sintética de la química sintética.
Sus antecedentes:
- La (-) -sordarina es un producto natural complejo con actividades biológicas potenciales.
- Las rutas sintéticas anteriores para la sordarina y sus análogos han sido limitadas.
- Una síntesis total robusta y eficiente es crucial para una mayor evaluación biológica y modificación estructural.
Objetivo del estudio:
- Para lograr la primera síntesis total de (-) -sordarina.
- Desarrollar nuevas metodologías sintéticas aplicables a la síntesis compleja de productos naturales.
- Establecer una ruta confiable para el acceso a la sordarina y sus derivados.
Principales métodos:
- Ag(I) - catalizó la ciclización del radical oxidativo de un derivado del ciclopropanol para formar un esqueleto de bicyclo[5.3.0]decan-3-one.
- La alilación intramolecular catalizada por Pd(0) para construir el marco biciclo[2.2.1]heptano-2-ón de la sordaricina.
- La dihidroxilación selectiva de los alquenos terminales mediante el uso de OsO ((4) y PhB ((OH) ((2).
- La glicosidación selectiva beta- 1,2-cis) facilitada por una asistencia 1,3-anquimérica de un grupo 4-metoxibenzoilo.
Principales resultados:
- Construcción exitosa del núcleo de las estructuras cíclicas de (-) -sordarina y sordaricina.
- Introducción eficiente y selectiva de grupos funcionales clave, incluidos los diolos y el enlace glucósido.
- Demostración de la utilidad de las estrategias sintéticas desarrolladas en la síntesis de moléculas complejas.
Conclusiones:
- Se ha logrado la primera síntesis total de (-) -sordarina.
- La vía sintética desarrollada es eficiente y utiliza nuevas reacciones clave.
- Este trabajo proporciona una plataforma valiosa para la síntesis de análogos de sordarina y productos naturales relacionados.
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