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Oxazinanonas tricíclicas altamente funcionales a través de la desaromatización oxidativa en pares y la

Steffen N Good¹, Robert J Sharpe¹, Jeffrey S Johnson¹

¹Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.

Journal of the American Chemical Society

|August 31, 2017

Resumen

Este estudio introduce un nuevo método para sintetizar estructuras heterotricíclicas complejas a partir de benzenoides simples. La nueva desaromatización oxidativa y la estrategia de cicloadición crean diversas arquitecturas moleculares, incluidos los intermedios para la síntesis de tetrodotoxina.

Área de la Ciencia:

Química orgánica
Química sintética
Química medicinal

Sus antecedentes:

Los benzenoides son materiales de partida abundantes pero difíciles para la síntesis de ciclohexano debido a su alta energía aromática.
Los métodos sintéticos existentes tienen limitaciones en el acceso a diversos ciclohexanos sustituidos a partir de benzenoides.

Objetivo del estudio:

Desarrollar una nueva vía sintética para estructuras heterotricíclicas previamente inaccesibles.
Demostrar un método para superar la aromaticidad inherente de los benzenoides para la síntesis de moléculas complejas.

Principales métodos:

Desaromatización oxidativa de los 2-hidroximetilfenoles
Deshidrogenación simultánea del N-hidroxicarbamato con un oxidante común.
Cicloadición de Acylnitroso Diels-Alder de especies reactivas generadas por pares.

Principales resultados:

Síntesis exitosa de nuevas estructuras heterotricíclicas.
Generación de [2.2.2]-oxazabiciclos con cuatro grupos funcionales ortogonales y tres estereocentros.
Diversidad demostrada en los productos intermedios derivados de la síntesis.

Conclusiones:

La metodología desarrollada proporciona acceso a andamios moleculares previamente desconocidos.
Este enfoque permite la síntesis rápida de intermediarios funcionalizados relevantes para productos naturales complejos como la tetrodotoxina.
La estrategia ofrece una nueva herramienta poderosa para la síntesis orgánica y el descubrimiento de fármacos.

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