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Síntesis total de la (+) -escolarisina A en su conjunto
Gregory L Adams1, Patrick J Carroll, Amos B Smith
1Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Journal of the American Chemical Society
|January 28, 2012
Resumen
Los investigadores lograron la síntesis total de (+) - escolarisina A, un producto natural complejo. Esta síntesis de 20 pasos establece la configuración absoluta de la molécula utilizando nuevas transformaciones químicas.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Síntesis de Productos Naturales.
- La estereoquímica es la estereoquímica.
Sus antecedentes:
- Scholarisine A es un producto natural arquitectónicamente complejo.
- Su actividad biológica y sus características estructurales requieren rutas sintéticas eficientes.
Objetivo del estudio:
- Para lograr la síntesis total de (+) - escolarisina A.
- Para asignar la configuración absoluta de la (+) -escolarisina A.
- Desarrollar nuevas metodologías sintéticas.
Principales métodos:
- Una secuencia sintética de 20 pasos.
- Ciclización reductiva de un nitrilo y un epoxido.
- Protocolo modificado de Fischer para el indole.
- Lactonización oxidativa en etapa tardía.
- Ciclización intramolecular para formar el núcleo de indolenina.
Principales resultados:
- Se ha logrado la síntesis total de la (+) -escolarisina A.
- Asignación de la configuración absoluta.
- Demostración de las transformaciones sintéticas clave.
Conclusiones:
- La estrategia sintética desarrollada es efectiva para la construcción de arquitecturas moleculares complejas.
- La síntesis proporciona acceso a la (+) -escolarisina A para una mayor investigación biológica.
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