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Síntesis total del (±) -maocristal V

Feng Peng¹, Samuel J Danishefsky

¹Department of Chemistry, Columbia University, New York, New York 10027, United States.

Journal of the American Chemical Society

|November 7, 2012

Resumen

La síntesis total del maoecristal racémico V se logró utilizando reacciones clave. Este estudio detalla un nuevo enfoque para la construcción de arquitecturas moleculares complejas.

Área de la Ciencia:

Química orgánica es la química orgánica.
Síntesis total de las respuestas.
Síntesis de Productos Naturales.

Sus antecedentes:

Maoecrystal V es un producto natural complejo con una estructura policíclica única.
Los esfuerzos sintéticos anteriores no han logrado la síntesis total de maoecristal V.

Objetivo del estudio:

Para lograr la primera síntesis total de maoecristal racémico V.
Desarrollar estrategias sintéticas eficientes para la construcción de moléculas policíclicas complejas.

Principales métodos:

Ciclización intramolecular Diels-Alder para ensamblar rápidamente el andamio del núcleo.
Reducción estereoselectiva para establecer la transfusión del anillo A-C.

Principales resultados:

Finalización exitosa de la síntesis total del maoecristal racémico V.
Demostración de un método robusto para la construcción del desafiante sistema de anillos trans-fusionados.

Conclusiones:

La ruta sintética desarrollada proporciona acceso al maoecristal V.
Los pasos clave de ciclización y reducción son aplicables a la síntesis de productos naturales relacionados.

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