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Síntesis total concisa de (-) jorunamicina A y (-) jorumicina habilitada por catálisis asimétrica
Eric R Welin1, Aurapat Ngamnithiporn1, Max Klatte1
1Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.
Science (New York, N.Y.)
|December 22, 2018
Resumen
Los investigadores desarrollaron una nueva estrategia sintética para los productos naturales de bis-tetrahidroisoquinolina (bis-THIQ), utilizando la catálisis de metales de transición en lugar de los métodos tradicionales. Este enfoque permite una síntesis eficiente y la creación de diversos análogos no naturales con propiedades anticancerígenas y antibióticas potenciales.
Área de la Ciencia:
- Síntesis de productos naturales
- Química orgánica
- Química medicinal
Sus antecedentes:
- Los compuestos de bis-tetrahidroisoquinolina (bis-THIQ) son conocidos por sus potentes actividades anticancerígenas y antibióticas.
- Las rutas sintéticas tradicionales a menudo emplean química aromática electrofílica, imitando las vías biosintéticas.
Objetivo del estudio:
- Desarrollar una nueva estrategia sintética para los productos naturales bis-THIQ, jorunnamicina A y jorumicina.
- Explorar una alternativa a la síntesis biomimética utilizando la catálisis moderna.
- Para permitir la preparación de diversos análogos no naturales.
Principales métodos:
- Utilizó la catálisis de metales de transición para eventos clave de formación de enlaces.
- Desarrolló una vía sintética de alta eficiencia (15 y 16 pasos para la jorunnamicina A y la jorumicina, respectivamente).
- Se apartó de las estrategias tradicionales basadas en la reacción de Pictet-Spengler.
Principales resultados:
- Con éxito sintetizó jorunnamicina A y jorumicina utilizando el nuevo enfoque catalítico.
- Se logra una alta eficiencia en el proceso sintético.
- Demostró una estrategia que rompe con la biomimética.
Conclusiones:
- La nueva estrategia catalizada por metales de transición ofrece una ruta eficiente para los productos naturales bis-THIQ.
- Este enfoque facilita la síntesis de una gama más amplia de análogos no naturales.
- Los hallazgos abren vías para explorar nuevos agentes terapéuticos basados en el andamio bis-THIQ.
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