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Síntesis total del chivosazol F en su totalidad
Tobias Brodmann1, Dominic Janssen, Markus Kalesse
1Centre for Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover, Schneiderberg 1b, D-30167 Hannover, Germany.
Journal of the American Chemical Society
|September 15, 2010
Resumen
Los investigadores informan de la primera síntesis de chivosazol F biológicamente activo. Este nuevo enfoque utiliza un acoplamiento intramolecular de Stille, superando los desafíos en la formación de macrolactona y confirmando la estructura propuesta de la molécula.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Síntesis de Productos Naturales.
Sus antecedentes:
- El chivosazol F es un producto natural de alta actividad biológica.
- La determinación estructural anterior se basó en RMN, métodos computacionales y análisis genético.
- Existieron desafíos en la síntesis de macrolactonas que contienen polieno debido a la isomerización.
Objetivo del estudio:
- Para lograr la primera síntesis total de chivosazol F. Para lograr la primera síntesis total de chivosazol F.
- Desarrollar una estrategia sintética que evite la isomerización del segmento tetraeno.
- Para confirmar la estructura propuesta de chivosazol F a través de la síntesis química.
Principales métodos:
- Acoplamiento intramolecular de Stille para la formación de macrolactona.
- Vía de síntesis orgánica en varios pasos.
- Técnicas espectroscópicas y analíticas para la confirmación estructural.
Principales resultados:
- El éxito de la síntesis de chivosazol F.
- El acoplamiento intramolecular de Stille efectivamente formó la macrolactona.
- La ruta sintética eludió la problemática isomerización de la fracción tetraeno.
- La síntesis validó la estructura propuesta anteriormente.
Conclusiones:
- Se logró la primera síntesis total de chivosazol F.
- El acoplamiento intramolecular de Stille es una estrategia viable para la construcción de macrolactonas complejas.
- La síntesis proporciona una prueba estructural definitiva para el chivosazol F.
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