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Síntesis total de los etnangios

Pengfei Li¹, Jun Li, Fatih Arikan

¹Institut für Organische Chemie, Ruprecht-Karls-Universität Heidelberg, INF 270, D-69120 Heidelberg, Germany.

Journal of the American Chemical Society

|August 4, 2009

Resumen

Los investigadores informan de la primera síntesis total de etnangien, un potente inhibidor de la ARN-polimerasa. Este estudio aclara el antibiótico macrolido.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química Medicinal La Química Medicinal es un campo de estudio de la química medicinal.
Biología Molecular Biología Molecular

Sus antecedentes:

Etnangien es un potente inhibidor de la ARN polimerasa.
La estructura compleja y la estereoquímica del antibiótico macrólido presentan un desafío sintético significativo.

Objetivo del estudio:

Para lograr la primera síntesis total de etnangien.
Establecer inequívocamente la configuración relativa y absoluta de los etnangios.
Desarrollar una ruta sintética modular y eficiente susceptible de diseño analógico.

Principales métodos:

Acoplamientos de aldol mediados por boro y estaño controlados por sustrato estereoselectivo para construir centros estereogénicos.
Macrociclado Heck de un sustrato conformacionalmente restringido para la formación de anillos.
Introducción en etapa tardía de una cadena lateral lábil.

Principales resultados:

Finalización exitosa de la primera síntesis total de etnangien.
Alta estereoselectividad y rendimiento logrado en reacciones de acoplamiento aldólico.
Se demostró una macrociclado eficiente y una funcionalización en etapa tardía.

Conclusiones:

La estrategia sintética descrita establece inequívocamente la configuración de etnangien.
El enfoque convergente y modular facilita la síntesis de análogos diseñados.
Este trabajo proporciona una base para una mayor exploración de la actividad biológica de los etnangios y sus derivados.

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