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Síntesis asimétrica en doce pasos del ácido (-) nodulispórico C
Nicole A Godfrey1, Devon J Schatz1, Sergey V Pronin1
1Department of Chemistry , University of California, Irvine , Irvine , California 92697-2025 , United States.
Journal of the American Chemical Society
|September 29, 2018
Resumen
Este estudio presenta una síntesis concisa y enantioselectiva del ácido (-) nodulispórico C. La ruta eficiente de 12 pasos utiliza policiclizaciones clave y ensamblaje convergente para el objetivo del indoloterpenoide.
Área de la Ciencia:
- Química orgánica
- Síntesis de productos naturales
Sus antecedentes:
- El ácido (-) nodulispórico C es un indoloterpenoide complejo con actividad biológica potencial.
- Las rutas sintéticas eficientes son cruciales para acceder a productos naturales tan complejos.
Objetivo del estudio:
- Desarrollar una síntesis corta y enantioselectiva del ácido (-) nodulispórico C.
- Demostrar la utilidad de nuevas metodologías sintéticas para la construcción de moléculas complejas.
Principales métodos:
- Síntesis enantioselectiva que emplea policiclizaciones diastereoselectivas.
- El ensamblaje convergente de una fracción de indol desafiante.
- Utilización de materiales de partida disponibles en el mercado para un enfoque simplificado.
Principales resultados:
- Se ha logrado una síntesis en 12 pasos del ácido (-) nodulispórico C.
- Se ha demostrado una alta diastereoselectividad en las etapas clave de la policiclización.
- Construido con éxito el núcleo terpenoide complejo y el fragmento de indenopyran.
Conclusiones:
- La vía sintética desarrollada es eficiente y enantioselectiva.
- La metodología es aplicable a la síntesis de otros indoloterpenos complejos.
- Este trabajo proporciona una vía valiosa para acceder al ácido (-) nodulispórico C.
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