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Síntesis total de ácido (-) -nahuóico C_i (B_ii)

Qi Liu¹, Yifan Deng¹, Amos B Smith¹

¹Department of Chemistry, Laboratory for Research on the Structure of Matter and Monell Chemical Senses Center, University of Pennsylvania , Philadelphia, Pennsylvania 19104, United States.

Journal of the American Chemical Society

|September 22, 2017

Resumen

Se sintetizó un nuevo policetido de cis-decalina, el ácido (-) nahuóico C, utilizando estrategias químicas avanzadas. Esta síntesis proporciona una nueva ruta para los productos naturales complejos de policetida.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales
Química de las policetidas

Sus antecedentes:

El ácido (-) -nahuoico C es un nuevo policetido de cis-decalina.
La estructura compleja de las policetidas presenta desafíos sintéticos significativos.

Objetivo del estudio:

Para lograr una síntesis total convergente de ácido (-) nahuóico C.
Desarrollar y aplicar nuevas metodologías sintéticas para la construcción de moléculas complejas.

Principales métodos:

Química de relés de aniones de tipo II (ARC) para la construcción de cadenas de poliol.
Reacción asimétrica de Diels-Alder catalizada por titanio para la formación de esqueletos de cis-decalina.
Acoplamiento alquino-alqueno dirigido por alcóxido de micalicio para la unión de fragmentos en etapa tardía.

Principales resultados:

Síntesis convergente total exitosa del ácido (-) nahuóico C (3).
Demostración de la utilidad del ARC y de las reacciones asimétricas de Diels-Alder en la síntesis de policetidos.
Se ha logrado un acoplamiento eficiente de fragmentos de gran tamaño en una fase tardía.

Conclusiones:

La vía sintética desarrollada es eficaz para acceder al ácido (-) nahuóico C.
Esta síntesis amplía el conjunto de herramientas para la construcción de productos naturales complejos de policetida.
Las estrategias empleadas ofrecen potencial para sintetizar moléculas relacionadas.

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