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Síntesis total asimétrica de (-) -crotonina G y (-) -crotonolida D

Hao Yu¹, Yutaro Hatano¹, Peng-Jui Chen¹

¹The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Journal of the American Chemical Society

|June 23, 2025

Resumen

Este estudio detalla las primeras síntesis totales enantioselectivas de crotonina G y crotonolida D, utilizando la ciclización radical mediada por SmI2 para la formación de carbono cuaternario complejo.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales

Sus antecedentes:

La crotonina G y la crotonolida D son productos naturales complejos con un interés biológico significativo.
Los esfuerzos sintéticos anteriores no han logrado una síntesis total enantioselectiva de estos compuestos.

Objetivo del estudio:

Para revelar las primeras síntesis totales enantioselectivas de crotonina G y crotonolida D.
Establecer una ruta sintética robusta que permita la construcción de productos naturales complejos.

Principales métodos:

Ciclización del radical cetilo mediada por SmI2 para la construcción de carbono cuaternario.
Escisión oxidativa de las olefinas para instalar estados de oxidación específicos.
Carbonización y oxidación catalizada por el paladio para el ensamblaje de la estructura del núcleo.

Principales resultados:

Síntesis total enantioselectiva exitosa de la crotonina G y el crotonolide D.
Construcción eficiente del centro de carbono cuaternario altamente congestionado.
Instalación de estados de oxidación C-19 y C-20 inusuales.

Conclusiones:

La estrategia sintética desarrollada proporciona acceso a productos naturales complejos.
La metodología destaca la utilidad de las ciclizaciones radicales mediadas por SmI2 en la síntesis de moléculas complejas.

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