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Síntesis total enantioselectiva de (+) -corimina y (-) -deformilcorimina

Benxiang Zhang¹, Xiaoqing Wang¹, Chaozhong Li^1,2

¹Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , P.R. China.

Journal of the American Chemical Society

|January 30, 2020

Resumen

Este estudio presenta la primera síntesis total enantioselectiva de los alcaloides de akuamilina (+) -corimina y (-) -deformilcorimina utilizando una estrategia de 11 pasos. El nuevo enfoque construye de manera eficiente los estereocentros clave y los sistemas de anillos para estos productos naturales complejos.

Área de la Ciencia:

Química orgánica
Química sintética
Síntesis de productos naturales

Sus antecedentes:

Los alcaloides de akuamilina son una clase de productos naturales complejos con actividades biológicas significativas.
La síntesis total de estos alcaloides presenta un desafío considerable debido a sus intrincadas estructuras y múltiples estereocentros.

Objetivo del estudio:

Se informará de la primera síntesis total enantioselectiva de (+) -corimina y (-) -deformilcorimina.
Desarrollar una estrategia sintética versátil aplicable a otros alcaloides de akuamilina.

Principales métodos:

Adición enantioselectiva catalizada por el cobre de malonato de dimetilo a un 3-bromooxindole.
Adición nucleofílica intramolecular de C y N para la construcción de anillos.
Ciclización de 7-endo promovida por níquel para la formación de anillos de azepanilo.

Principales resultados:

Síntesis exitosa de (+) -corimina y (-) -deformilcorimina en 11 pasos a partir de la N-nosiltriptamina.
Se ha establecido un estereocentro clave de carbono cuaternario en C7.
Demostró la utilidad de la estrategia mediante la síntesis de tres derivados adicionales de la akuamilina.

Conclusiones:

La vía sintética desarrollada es eficiente y enantioselectiva.
La estrategia proporciona una plataforma sólida para el acceso a diversos alcaloides de akuamilina.
Este trabajo amplía la accesibilidad sintética de productos naturales biológicamente relevantes.

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