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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
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Anulación Desimétrica Diastereodivergente para el Acceso Spirooxindoles: sondas químicas para la mitosis
Yu-Hua Wen1, Fengrui Yang2, Shuai Li1
1Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
Journal of the American Chemical Society
|February 13, 2023
Resumen
Los investigadores desarrollaron un nuevo método catalítico para crear lactonas espirooxindoles complejas con un alto control estereoquímico. Este avance permite la síntesis de posibles fármacos candidatos con actividades antiproliferativas significativas.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Química medicinal
Sus antecedentes:
- Los espirooxindoles son andamios clave para los compuestos biológicamente activos.
- El desarrollo de métodos para la síntesis diastereodivergente de espirooxindoles con control sobre múltiples centros quirales, incluidos los cuaternarios, sigue siendo un desafío.
Objetivo del estudio:
- Informar de una nueva anulación desimétrica diastereodivergente [3 + 3] para la construcción de lactonas espirooxindoles enantioméricamente enriquecidas.
- Para lograr el control total sobre los centros quirales continuos, incluyendo un centro estereogénico cuaternario de carbono.
Principales métodos:
- Se utilizó la catálisis cooperativa N-heterocíclica (NHC) / Rh para la anulación de alquenos oxabicíclicos con enalos.
- Se empleó un sistema de catalizador combinado en el que un complejo de rodio y un catalizador NHC controlaban independientemente la estereoquímica en diferentes centros.
Principales resultados:
- Se obtienen excelentes enantioselectividades (hasta > 99% ee) y diastereoselectividades (hasta > 95:5 dr).
- Demostró la capacidad de acceder a cuatro estereoisómeros cambiando las configuraciones del catalizador.
- Sintetizó compuestos útiles de las espirooxindolas quirales.
- Se observaron potentes actividades antiproliferativas contra las células HeLa, con compuestos que detienen las células en mitosis.
Conclusiones:
- Se estableció una síntesis diastereodivergente asimétrica catalítica sin precedentes de las lactonas espirooxindoles.
- Se destacó el impacto significativo de las configuraciones absolutas y relativas en las bioactividades.
- Enfatizó la importancia de este método para explorar las relaciones estructura-actividad y desarrollar nuevos agentes terapéuticos.
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