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Un enfoque convergente para los alcaloides ciclopéptidos: síntesis total de sanjoinina G1
Taoues Temal-Laïb1, Jacqueline Chastanet, Jieping Zhu
1Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France.
Journal of the American Chemical Society
|January 24, 2002
Resumen
Los investigadores desarrollaron una nueva síntesis para alcaloides ciclopéptidos con un enlace de éter de arilo-alquilo utilizando una reacción intramolecular S(N) Ar. Este método sintetizó con éxito el producto natural sanjoinina G1.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química Medicinal La Química Medicinal es un campo de estudio de la química medicinal.
- Síntesis de Productos Naturales.
Sus antecedentes:
- Los alcaloides ciclopéptidos son una clase de productos naturales con diversas actividades biológicas.
- La síntesis de alcaloides ciclopéptidos que contienen un enlace endocíclico de éter arilo-alquilo presenta un desafío significativo.
- Las estrategias sintéticas existentes a menudo carecen de eficiencia o amplia aplicabilidad.
Objetivo del estudio:
- Desarrollar una estrategia general y eficiente para la síntesis de alcaloides ciclopéptidos con un enlace endocíclico de éter arilo-alquilo.
- Investigar el papel del grupo protector N-terminal en el éxito de la estrategia sintética.
- Para sintetizar el alcaloide ciclopéptido natural sanjoinina G1 utilizando el método desarrollado.
Principales métodos:
- Desarrollo de una nueva estrategia sintética centrada en una reacción intramolecular de S ((N) Ar.
- Evaluación sistemática de diferentes grupos protectores N-terminales para optimizar el paso clave de ciclización.
- Síntesis paso a paso de la sanjoinina G1 a partir de precursores de aminoácidos fácilmente disponibles.
Principales resultados:
- Se estableció una estrategia general para la síntesis de alcaloides ciclopéptidos con un enlace endocíclico de arilo-alquilo éter.
- Se demostró el papel crucial del grupo protector N-terminal en la facilitación de la reacción S(N) Ar intramolecular.
- El producto natural sanjoinina G1, un paraciclófano de 14 miembros, fue sintetizado con éxito en siete pasos.
- Se logró un rendimiento general del 21% para la síntesis de sanjoinina G1.
Conclusiones:
- La estrategia sintética desarrollada proporciona una ruta versátil a los alcaloides ciclopéptidos que contienen un enlace endocíclico de arilo-alquilo éter.
- El grupo protector N-terminal es un determinante crítico para el éxito de este enfoque sintético.
- La síntesis de sanjoinina G1 valida la utilidad y eficiencia de la nueva metodología para la síntesis de productos naturales.
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