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Síntesis total asimétrica del 4β-acetoxiprobotriano-9β,15α-diol de alta tensión

Wen Zhang^1,2, Zi-Xiong Zhou¹, Xu-Jiang Zhu¹

¹Shenzhen Grubbs Institute, Department of Chemistry, Guangdong Provincial Key Laboratory of Catalytic Chemistry, Southern University of Science and Technology, Shenzhen 518055, China.

Journal of the American Chemical Society

|November 11, 2020

Resumen

Se logró la primera síntesis asimétrica de un producto natural complejo con un núcleo de biciclo [3.3.0] octano tensado. Este estudio demuestra la construcción eficiente de siete estereocentros utilizando reacciones de cicloadición y reordenamiento catalizadas por rodio.

Área de la Ciencia:

Química orgánica
Química sintética
Síntesis de productos naturales

Sus antecedentes:

La síntesis de productos naturales complejos es crucial para comprender su actividad biológica.
Los sistemas de anillos de alta tensión presentan desafíos sintéticos significativos.
El 4β-acetoxiprobotriano-9β,15α-diol contiene un núcleo de biciclo [3.3.0] octano transfundido raro.

Objetivo del estudio:

Para lograr la primera síntesis total asimétrica de 4β-acetoxiprobotriano-9β,15α-diol.
Desarrollar un método eficiente y diastereoselectivo para la construcción del sistema tricíclico [6-5-5].
Para instalar siete estereocentros contiguos con alta fidelidad.

Principales métodos:

Reacción de cicloadición asimétrica catalizada por el rodio [4 + 2].
Reorganización del tipo ácido bencílico en condiciones suaves.
Instalación estereoselectiva de siete estereocentros contiguos.

Principales resultados:

El éxito y la primera síntesis total asimétrica de 4β-acetoxyprobotryane-9β,15α-diol.
Construcción eficiente y diastereoselectiva del sistema de anillo de biciclo [3.3.0] octano transfundido.
El alto control estéreo se logró mediante la instalación de siete estereocentros contiguos.

Conclusiones:

La estrategia sintética desarrollada es eficaz para la construcción de moléculas policíclicas complejas.
El estudio proporciona una nueva ruta a un esqueleto de productos naturales raros y tensos.
Este trabajo avanza en el campo de la síntesis asimétrica y la química de productos naturales.

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