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Síntesis total de la (-) -isosichizogamina fue obtenida
Yusuke Miura1, Noriyuki Hayashi, Satoshi Yokoshima
1Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Journal of the American Chemical Society
|July 12, 2012
Resumen
Se logró la primera síntesis total asimétrica de (-) -isoschizogamina. Los pasos clave incluyeron un reordenamiento de Wagner-Meerwein y una metátesis en tándem para la construcción de un marco de carbono eficiente.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Síntesis de Productos Naturales.
Sus antecedentes:
- (-) La isoschizogamina es un producto natural complejo.
- Las rutas sintéticas eficientes son cruciales para acceder a tales moléculas.
Objetivo del estudio:
- Para lograr la primera síntesis total asimétrica de (-) -isoschizogamina.
- Desarrollar una estrategia sintética fácil y eficiente.
Principales métodos:
- Reorganización de Wagner-Meerwein para la construcción del marco de carbono.
- Reacciones de metátesis en tándem y de cierre de anillo.
- Adición estereoselectiva de ácido arilborónico mediada por el rodio con adición de 1,4.
- Ciclización del éter hemiaminal.
Principales resultados:
- Construcción exitosa del esqueleto de carbono de la (-) -isoschizogamina.
- Demostración de las transformaciones sintéticas clave, incluidos los reordenamientos y las metástasis.
- Establecimiento de un control estereoquímico durante toda la síntesis.
Conclusiones:
- Se informa de la primera síntesis total asimétrica de (-) -isoschizogamina.
- La ruta sintética desarrollada es eficiente y destaca aplicaciones novedosas de reacciones clave.
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