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Síntesis estereocontrolada de la (-) -bactobolina A

Petra Vojáčková^1,2, Lucyna Michalska^1,2, Marek Nečas¹

¹Department of Chemistry, Masaryk University, Brno 625 00, Czech Republic.

Journal of the American Chemical Society

|April 15, 2020

Resumen

En este estudio se informa de una síntesis estereoselectiva del antibiótico antitumoral (-) - bactobolina A. La nueva ruta utiliza el ácido (-) -quínico y las reacciones clave para construir la molécula, obteniendo 90 mg del compuesto objetivo.

Área de la Ciencia:

Síntesis orgánica
Química medicinal
Biología Química

Sus antecedentes:

(-) - Bactobolina A es un antibiótico que se une a los ribosomas y tiene propiedades antitumorales.
Su compleja estructura presenta un desafío sintético significativo.
La síntesis eficiente y estereoselectiva es crucial para una mayor evaluación biológica.

Objetivo del estudio:

Desarrollar una vía sintética estereoselectiva para la (-) bactobolina A.
Para establecer los cinco estereocentros contiguos del antibiótico.
Proporcionar un método escalable para la producción de (-) bactobolina A.

Principales métodos:

Se utiliza el ácido (-) -quínico como material de partida de la piscina quiral.
Se ha empleado una reacción estereoselectiva de vinilo-aldol para la introducción de sustituyentes de diclorometilo.
Aplicación de la aminación C-H catalizada por el rodio diastereoselectivo para la configuración de aminas axiales.
Alcoxicarbonización intramolecular incorporada para la formación de lactona cíclica.

Principales resultados:

Se ha sintetizado con éxito (-) - bactobolina A trifluoroacetato.
Se logró un rendimiento global del 10% para la vía sintética.
Preparado 90 mg del producto final, demostrando la viabilidad.
Establecido cinco estereocentros contiguos con alto control estéreo.

Conclusiones:

Se desarrolló una nueva y eficiente síntesis estereoselectiva de (-) - bactobolina A.
La estrategia sintética utiliza efectivamente los materiales iniciales de la piscina quiral y las reacciones estereocontroladas clave.
Este trabajo proporciona una vía viable para acceder a la (-) bactobolina A para futuras investigaciones.

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