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Síntesis total de salimabromida: un policetido tetraciclico de una mixobacterium marina
Matthias Schmid1,2, Adriana S Grossmann1, Klaus Wurst3
1Department of Chemistry , Ludwig-Maximilians-University Munich , Butenandtstrasse 5-13 , 81377 Munich , Germany.
Journal of the American Chemical Society
|June 29, 2018
Resumen
Los científicos sintetizaron el salimabromuro, un antibiótico poliquetídeo único de las bacterias marinas. Este logro proporciona una ruta escalable a esta molécula compleja con un marco tetraciclico sin precedentes.
Área de la Ciencia:
- Química orgánica
- Síntesis de productos naturales
- Microbiología marina
Sus antecedentes:
- La salimabromida es un complejo antibiótico policetídeo previamente aislado de Enhygromyxa salina.
- Su estructura tetraciclica es densamente funcional y conformacionalmente rígida, lo que representa un nuevo marco de producto natural.
Objetivo del estudio:
- Para reportar la primera síntesis química total de la salimabromida.
- Para establecer una ruta sintética robusta y escalable a este producto natural sin precedentes.
Principales métodos:
- Empleando una serie de transformaciones químicas bien orquestadas y robustas.
- Utilizando un reordenamiento de Wagner-Meerwein promovido por el ácido / ciclo de Friedel-Crafts para construir centros de carbono cuaternarios.
- Implementación de una adición de ciclo [2+2] mediada por ketiminio para la síntesis estereoselectiva.
Principales resultados:
- Se logró una síntesis total exitosa de salimabromida.
- La síntesis construyó eficientemente el complejo marco tetraciclico, que incluye dos centros de carbono cuaternarios adyacentes.
- Se establecieron múltiples estereocentros simultáneamente utilizando una reacción clave de cicloadición.
Conclusiones:
- La primera síntesis química de salimabromida demuestra la viabilidad de acceder a este complejo producto natural.
- La estrategia sintética desarrollada proporciona una base para una mayor exploración y derivación de salimabromida.
- Este trabajo amplía el kit de herramientas del químico sintético para la construcción de estructuras poliquetidas intrincadas.
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