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El propeno como eje atómico-económico para la síntesis total concisa de polienos: Piericidina A

Barry M Trost¹, Hadi Gholami¹

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

Journal of the American Chemical Society

|September 4, 2018

Resumen

Los investigadores desarrollaron una síntesis concisa para la piericidina A utilizando propeno como eje para unir fragmentos de alquina. Este método crea eficientemente estructuras complejas de 1,3,6-trieno, ofreciendo una nueva estrategia para la síntesis de productos naturales.

Área de la Ciencia:

Química orgánica
Química sintética
Síntesis de productos naturales

Sus antecedentes:

La piericidina A es un producto natural biológicamente activo.
Las rutas sintéticas existentes pueden ser largas e ineficientes.
El desarrollo de nuevas estrategias sintéticas es crucial para acceder a moléculas complejas.

Objetivo del estudio:

Dar a conocer una síntesis total concisa y convergente de la piericidina A.
Introducir una nueva metodología sintética que utilice el propeno como elemento clave.
Para demostrar la versatilidad de este enfoque para la síntesis de compuestos que contienen 1,3,6-trieno.

Principales métodos:

Utilizando propeno como un eje sintético para el acoplamiento secuencial de alquinos.
Empleando una estrategia convergente para ensamblar estructuras moleculares complejas.
Desarrollo de una estrategia de formación de enlaces C-C con una alta economía atómica.

Principales resultados:

Síntesis total exitosa y concisa de la piericidina A.
Demostración de la utilidad del propeno en la formación de motivos de 1,3,6-trieno.
Síntesis eficiente de varios compuestos poliinsaturados complejos a partir de alquinas simples.

Conclusiones:

La estrategia sintética desarrollada ofrece un paradigma ortogonal para la formación de enlaces C-C.
Este enfoque mejora la economía de pasos y la eficiencia en la síntesis de productos naturales poliinsaturados.
La metodología proporciona una herramienta valiosa para acceder a moléculas orgánicas complejas.

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