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Síntesis enantioselectiva de (+) -Lucidumone en la escala de gramos

Guanghao Huang¹, Cyrille Kouklovsky¹, Aurélien de la Torre¹

¹Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Saclay, CNRS, 15 rue Georges Clémenceau, 91405 Orsay, Cedex, France.

Journal of the American Chemical Society

|September 23, 2022

Resumen

La primera síntesis total enantioselectiva de (+) -lucidumone se logró en 13 pasos. Este método escalable produjo más de un gramo del producto natural, demostrando su eficiencia.

Área de la Ciencia:

Química orgánica
Síntesis total
Síntesis asimétrica

Sus antecedentes:

El (+) -Lucidumone es un producto natural con un potencial significado biológico.
Las rutas sintéticas eficientes y enantioselectivas son cruciales para acceder a los productos naturales.
Las síntesis anteriores pueden haber carecido de escalabilidad o enantioselectividad.

Objetivo del estudio:

Desarrollar la primera síntesis total enantioselectiva de (+) -lucidumone.
Establecer una vía sintética escalable y eficiente para la síntesis de productos naturales.
Explorar las transformaciones químicas clave para la construcción de arquitecturas moleculares complejas.

Principales métodos:

Cicloadición de Diels-Alder enantioselectiva inversa a la demanda de electrones para la formación de lactona bicíclica puenteada.
Formación de enlaces C-O para el ensamblaje de fragmentos.
Una cascada de retro- [4 + 2] / [4 + 2] cicloadición de una olla.

Principales resultados:

Se ha logrado la síntesis total enantioselectiva en 13 pasos de (+) -lucidumone.
Demostración de la escalabilidad con más de un gramo producido en un solo lote.
Los pasos clave incluyeron una nueva cascada de cicloadición y un acoplamiento eficiente de fragmentos.

Conclusiones:

La vía sintética descrita es la primera vía enantioselectiva hacia el (+) -lucidumone.
La síntesis es escalable y eficiente, adecuada para la producción a gran escala.
La metodología proporciona un enfoque valioso para la síntesis de productos naturales relacionados.

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