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Síntesis total de la (+) -saraína A
Michael H Becker1, Peter Chua, Robert Downham
1Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Journal of the American Chemical Society
|September 14, 2007
Resumen
Los investigadores lograron la primera síntesis total enantioselectiva del alcaloide marino saraína A. Esta molécula compleja de moléculas.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Síntesis de Productos Naturales.
- Química Medicinal La Química Medicinal es un campo de estudio de la química medicinal.
Sus antecedentes:
- Sarain A es un alcaloide marino complejo con actividad biológica potencial.
- Los esfuerzos sintéticos anteriores no han logrado una síntesis total enantioselectiva.
Objetivo del estudio:
- Desarrollar una nueva y eficiente síntesis total enantioselectiva de (+) -saraína A. novel y eficiente.
- Explorar nuevas metodologías sintéticas para la construcción de estructuras complejas de alcaloides.
Principales métodos:
- Adición asimétrica de Michael para la instalación de estereocentro.
- Ciclización de iones de enoxisilano-N-sulfoniliminio para el estereocentro de carbono cuaternario.
- Metátesis de cierre de anillo y acoplamiento intramolecular de Stille para la formación de macrociclos.
Principales resultados:
- El éxito de la síntesis total enantioselectiva de (+) -saraína A.
- Construcción del núcleo de diazatricicloundecano.
- Formación del macrociclo insaturado de 14 miembros.
Conclusiones:
- La ruta sintética desarrollada es eficiente y versátil.
- Esta síntesis proporciona una plataforma para una mayor derivación y evaluación biológica de los análogos de la saraína A.
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