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Síntesis totales de (+) -ineleganolida y (-) -sinulocmodina C

Joseph P Tuccinardi¹, John L Wood¹

¹Department of Chemistry and Biochemistry, Baylor University, One Bear Place 97348, Waco, Texas 76798, United States.

Journal of the American Chemical Society

|October 25, 2022

Resumen

Los investigadores lograron la primera síntesis total de productos naturales nor-furanocembranoides (+) -ineleganolida y (-) -sinulocmodina C. Una nueva estrategia empleó Michael transannular y ciclizaciones radicales para la construcción eficiente de estas moléculas complejas.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales
Química medicinal

Sus antecedentes:

Los nor-furanocembranoides son una clase de productos naturales marinos con actividades biológicas potenciales.
La síntesis total de estas moléculas complejas presenta desafíos significativos debido a sus estructuras intrincadas.

Objetivo del estudio:

Se comunicarán las primeras síntesis totales de (+) -ineleganolida y (-) -sinulocmodina C.
Desarrollar una estrategia sintética eficiente y versátil para los productos naturales nor-furanocembranoides.

Principales métodos:

Un enfoque sintético convergente que utiliza una reacción Michael transanular.
Ciclización radical diastereoselectiva para construir un intermediario de lactona cíclico clave.
Ciclización de Nozaki-Hiyama-Kishi y una cascada de oxidación de furano de un solo recipiente / oxa-Michael para la macrociclización.

Principales resultados:

Se lograron síntesis totales exitosas y eficientes de (+) -ineleganolida y (-) -sinulocmodina C.
Se utilizó un intermediario macrocíclico común para la preparación de ambos productos naturales.
Se superaron los principales desafíos estereoquímicos a través del diseño estratégico de la reacción.

Conclusiones:

La estrategia sintética desarrollada proporciona una ruta sólida hacia los productos naturales nor-furanocembranoides.
Este trabajo amplía la accesibilidad de estos compuestos para una mayor investigación biológica.
El estudio pone de relieve la importancia del control estereoquímico en la síntesis de moléculas complejas.

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