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Síntesis total de la (±) aspergilina A

Mina C Nakhla¹, John L Wood¹

¹Department of Chemistry and Biochemistry, Baylor University , One Bear Place 97348, Waco, Texas 76798, United States.

Journal of the American Chemical Society

|December 14, 2017

Resumen

Se logró la síntesis total de aspergilina A. Los pasos clave involucraron la formación de una nueva pirrolinona y una cicloadición [3+2] formal para construir la molécula compleja.

Área de la Ciencia:

Química orgánica
Química sintética

Sus antecedentes:

La aspergilina A es un producto natural complejo con actividad biológica potencial.
Las rutas sintéticas eficientes son cruciales para acceder y estudiar tales moléculas.

Objetivo del estudio:

Para describir la primera síntesis total de (±) -aspergilina A.
Desarrollar nuevas metodologías sintéticas aplicables a la construcción de moléculas complejas.

Principales métodos:

Formación de anillo de pirrolidinon que utiliza una amina de propargilo y un enolato de amonio derivado del cloruro de metilmalonilo.
Una reacción formal de cicloadición [3+2] que emplea un imidato y una ciclopropenona.

Principales resultados:

Ejecución exitosa de la síntesis total de (±) -aspergilina A.
Demostración de la utilidad de las estrategias de formación y cicloadición de pirrolinona desarrolladas.

Conclusiones:

La vía sintética descrita proporciona acceso a la (±) aspergilina A.
Las metodologías empleadas representan valiosas adiciones al kit de herramientas del químico sintético para la construcción de estructuras heterocíclicas complejas.

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