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Síntesis total del ácido kadcoccínico un éster trimetilo

Barry M Trost¹, Guoting Zhang¹, Hadi Gholami¹

¹Department of Chemistry, Stanford University, Stanford, California 94305-5580, United States.

Journal of the American Chemical Society

|July 29, 2021

Resumen

Los científicos lograron la primera síntesis total del éster trimetilo A del ácido kadcoccínico. Este nuevo enfoque utiliza una formación de ciclopentenona catalizada por oro y una adición conjugada mediada por cobre para construir el esqueleto del producto natural.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales

Sus antecedentes:

El ácido kadcoccínico A es un producto natural complejo con una estructura química única.
La síntesis total de productos naturales es crucial para comprender su actividad biológica y para desarrollar nuevas metodologías sintéticas.

Objetivo del estudio:

Para describir la primera síntesis total del éster trimetilo del ácido kadcoccínico A.
Desarrollar una estrategia sintética general para el acceso a productos naturales relacionados.

Principales métodos:

Cíclicación catalizada por oro de un acetato de enil para formar un andamio de ciclopentenona.
Adición de conjugado mediada por cobre y reacción de Conio catalizado por oro para ensamblar el esqueleto del producto natural.
Se investigó el control estereoquímico en la formación de ciclopentenona.

Principales resultados:

Síntesis total exitosa del éster trimetilo A del ácido kadcoccínico.
Se demostró el papel crucial de la estereoquímica del acetato de enil en la formación regioselectiva de ciclopentenona.
Estableció un método eficiente para construir el anillo D del producto natural.

Conclusiones:

La estrategia sintética reportada proporciona una plataforma versátil para la síntesis de análogos del ácido kadcoccínico A.
Este trabajo amplía el repertorio de herramientas sintéticas para la síntesis de productos naturales complejos.

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