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Síntesis total asimétrica de la (+) -Alstonlarsina A

Jun-Jun Yao¹, Rui Ding¹, Xiaoming Chen^1,2

¹The State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Nano-Micro Materials Research, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055, China.

Journal of the American Chemical Society

|July 27, 2022

Resumen

Los científicos lograron la primera síntesis total asimétrica de (+) - alstonlarsina A. Los pasos clave incluyeron alquilación alilica asimétrica, cicloadición de óxido de nitrilo-alqueno y una reacción de Pictet-Spengler interrumpida para construir la molécula compleja.

Área de la Ciencia:

Química orgánica
Química sintética
Química medicinal

Sus antecedentes:

La alstonlarsina A es un producto natural complejo con una estructura policíclica única.
El desarrollo de rutas sintéticas eficientes para moléculas complejas es crucial para el descubrimiento de fármacos y la biología química.

Objetivo del estudio:

Para lograr la primera síntesis total asimétrica de (+) -alstonlarsina A.
Desarrollar nuevas metodologías sintéticas para la construcción de arquitecturas moleculares complejas.

Principales métodos:

Alquilación alilica asimétrica catalizada por el paladio para establecer el estereocentro C15.
La cicloadición intramolecular de óxido de nitrilo-alqueno [3 + 2] (INOC [3 + 2]) para la construcción de la columna vertebral de ciclohepta[b]indoles y la instalación del centro cuaternario C20.
Reacción de Pictet-Spengler interrumpida en etapa tardía (IPSR) para el montaje rápido de la estructura del núcleo.

Principales resultados:

Se ha completado con éxito la primera síntesis asimétrica total de (+) -alstonlarsina A.
Demostración de nuevas aplicaciones de la alquilación alilica catalizada por Pd, INOC [3 + 2] e IPSR en la síntesis de moléculas complejas.
Establecimiento de estereocentros clave, incluido un complejo centro cuaternario de carbono.

Conclusiones:

La estrategia sintética desarrollada proporciona una ruta eficiente hacia la (+) -alstonlarsina A.
Las metodologías empleadas ofrecen herramientas valiosas para la síntesis de otros productos naturales complejos y fármacos candidatos.
Esta síntesis avanza en el campo de la síntesis asimétrica y la química de productos naturales.

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