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Síntesis total enantioselectiva de (-) - incarviatona A

Benke Hong^1,2, Chao Li¹, Zhen Wang³

¹Beijing National Laboratory for Molecular Sciences, Department of Chemical Biology, College of Chemistry and Molecular Engineering, Synthetic and Functional Biomolecules Center, and Peking-Tsinghua Center for Life Sciences, Peking University , Beijing 100871, China.

Journal of the American Chemical Society

|September 16, 2015

Resumen

La primera síntesis total de (-) -incarviatona A se logró en 14 pasos utilizando la funcionalización C-H escalable y una cascada biomimética. Este proceso eficiente ensambla rápidamente el marco de dialdehído de indanilo para la síntesis de productos naturales.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales

Sus antecedentes:

El (-) -incarviatón A es un producto natural complejo.
Las rutas sintéticas eficientes son cruciales para acceder a tales moléculas.

Objetivo del estudio:

Se comunicará la primera síntesis total de (-) -incarviatona A.
Desarrollar una estrategia sintética escalable y eficiente.

Principales métodos:

Síntesis de 14 pasos a partir del ácido fenilacético.
Funcionalización C-H escalable y secuencial para el ensamblaje del marco.
Estrategia de cascada biomimética para la formación de un producto natural en un solo recipiente.

Principales resultados:

Se ha logrado la síntesis total de (-) -incarviatona A.
Ensamblaje rápido del marco de dialdehído de indanilo.
Demostración de una cascada biomimética de un solo recipiente para la síntesis de productos naturales.

Conclusiones:

La ruta sintética desarrollada es eficiente y escalable.
La cascada biomimética ofrece una poderosa estrategia para la síntesis de productos naturales.
Se obtuvieron conocimientos mecanicistas detallados sobre el proceso en cascada.

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