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Síntesis total y asignación estereoquímica del calispongiolido
Jingjing Zhou1, Bowen Gao1, Zhengshuang Xu1
1Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Xili, Nanshan District, Shenzhen 518055, China.
Journal of the American Chemical Society
|May 27, 2016
Resumen
La síntesis total de los estereoisómeros de los callispongiolidos definió con precisión su estructura. El núcleo de macrolactona
Área de la Ciencia:
- Química orgánica
- Química medicinal
- Síntesis Química
Sus antecedentes:
- Los calispongiolidos son productos naturales con propiedades anticancerígenas potenciales.
- La estereoquímica precisa de los callispongiolidos es crucial para su actividad biológica.
- Los estudios previos no han aclarado completamente los requisitos estereocímicos para la actividad de la callispongiolida.
Objetivo del estudio:
- Para lograr la síntesis total de cuatro estereoisómeros de caliespongiólidos.
- Para asignar inequívocamente la estereocímica relativa y absoluta de los callispongiolidos.
- Evaluar el impacto de la estereoquímica en la actividad anticancerígena de los callispongiolidos.
Principales métodos:
- Se diseñó una ruta sintética convergente y estereocontrolada.
- Las reacciones clave incluyeron la alilación de Krische, la reacción de Kiyooka Aldol, la olefinación de Kociénski-Julia, la olefinación de Still-Gennari, la macrociclización de Yamaguchi y el acoplamiento de Sonogashira.
- Los estereoisómeros sintetizados se evaluaron biológicamente contra varias líneas celulares cancerosas.
Principales resultados:
- Se sintetizaron con éxito cuatro estereoisómeros distintos de callispongiolida.
- La ruta sintética proporcionó una asignación inequívoca de la estereoquímica relativa y absoluta.
- La evaluación biológica demostró que la estereoquímica del núcleo de macrolactona influye significativamente en la actividad anticancerígena.
Conclusiones:
- La síntesis total estableció la estructura estereoquímica definitiva de los callispongiolidos.
- La estereoquímica es un determinante crítico de la eficacia de la callispongiolida contra las células cancerosas.
- Este trabajo proporciona una base para el desarrollo de análogos de callispongiolida optimizados estereoquímicamente.
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