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Síntesis total de (-) -cromodorolido B

Daniel J Tao¹, Yuriy Slutskyy¹, Larry E Overman¹

¹Department of Chemistry, 1102 Natural Sciences II, University of California , Irvine, California 92697-2025, United States.

Journal of the American Chemical Society

|February 17, 2016

Resumen

Se logró la primera síntesis total de un diterpenoide de cromodorolida. Una nueva reacción en cascada radical construyó eficientemente enlaces clave carbono-carbono y estereocentros para el cromodorolido B.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales

Sus antecedentes:

Los cromodorolidos son diterpenoides complejos con actividad biológica potencial.
La síntesis total de estos compuestos presenta desafíos químicos significativos.

Objetivo del estudio:

Para lograr la primera síntesis total de un diterpenoide cromodorolido.
Desarrollar una estrategia sintética eficiente para la construcción de la estructura del núcleo del cromodorolido.

Principales métodos:

Utilizando una reacción en cascada de adición/ciclización/fragmentación de radicales bimoleculares.
Uniendo fragmentos de butenolido y transhidrindano.
Formación estereoselectiva de múltiples estereocentros contiguos.

Principales resultados:

Se ha sintetizado con éxito un diterpenoide cromodorolide.
Estableció una nueva reacción en cascada para la formación de enlaces C-C.
Se generaron estereoselectivamente tres de los diez estereocentros en el cromodorolide B.

Conclusiones:

La vía sintética descrita proporciona una vía viable para los cromodorolidos.
La cascada de radicales desarrollada es una herramienta poderosa para la síntesis de moléculas complejas.
Este trabajo sienta las bases para acceder a otros análogos de cromodorolida.

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