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Síntesis totales basadas en catálisis de pateamina A y DMDA-Pat A
Chun-Xiang Zhuo1, Alois Fürstner1
1Max-Planck-Institut für Kohlenforschung , D-45470 Mülheim/Ruhr , Germany.
Journal of the American Chemical Society
|July 31, 2018
Resumen
Una nueva síntesis de pateamina A y su análogo DMDA-Pat A proporciona estos compuestos citotóxicos para la investigación. El método utiliza una nueva reacción catalizada por hierro para crear una estructura de dienoato clave, lo que permite una producción escalable para el descubrimiento de fármacos.
Área de la Ciencia:
- Química de los productos naturales marinos
- Síntesis orgánica
- Química medicinal
Sus antecedentes:
- La pateamina A y el DMDA-Pat A son compuestos citotóxicos potentes.
- Estos compuestos son prometedores para el tratamiento del melanoma y la caquexia.
- El suministro limitado ha obstaculizado la evaluación biológica detallada.
Objetivo del estudio:
- Desarrollar una nueva vía sintética escalable para la pateamina A y el DMDA-Pat A.
- Para permitir una mayor evaluación biológica y el desarrollo de fármacos.
Principales métodos:
- Una estrategia poco ortodoxa usando un intermediario de 2 pironas.
- Apertura de anillo catalizado por hierro/acoplamiento cruzado para formar el Z,E-dienoato.
- La catálisis de oro para la síntesis de precursores y el acoplamiento de Stille para la formación de cadenas laterales.
Principales resultados:
- Se logró una síntesis corta, robusta y escalable de pateamina A y DMDA-Pat A.
- La estrategia construyó de manera eficiente la desafiante subestructura de dienoato.
- La síntesis podría ser redirigida fácilmente de la pateamina A a la DMDA-Pat A.
Conclusiones:
- La vía sintética desarrollada supera las limitaciones de suministro de pateamina A y sus análogos.
- Este trabajo facilita una mayor investigación de su potencial terapéutico.
- Las ideas mecánicas se obtuvieron al estudiar los complejos de pirona tricarbonilirona.
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