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Síntesis total de la (+) -11,11'-dideoxyverticilina A, también conocida como A-dioxyverticilina
Justin Kim1, James A Ashenhurst, Mohammad Movassaghi
1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Science (New York, N.Y.)
|April 11, 2009
Resumen
Los investigadores lograron la primera síntesis total del complejo alcaloide fúngico (+) -11,11'-dideoxyverticilina A. Este avance proporciona una nueva estrategia para la síntesis de productos naturales relacionados con la epidithiodiketopiperazina.
Área de la Ciencia:
- Química de Productos Naturales Química de Productos Naturales
- Síntesis orgánica La síntesis orgánica.
- Microbiología marina Microbiología marina.
Sus antecedentes:
- El metabolito fúngico (+) -11,11'-dideoxyverticillin A es un alcaloide citotóxico.
- Pertenece a la familia dimérica epidithiodiketopiperazina, conocida por su complejidad estructural.
- A pesar de ser conocidos desde hace décadas, ningún miembro de esta familia ha sido sintetizado totalmente.
Objetivo del estudio:
- Para lograr la primera síntesis total enantioselectiva de (+) -11,11'-dideoxyverticilina A. fue obtenido.
- Desarrollar una estrategia sintética inspirada en la vía biosintética propuesta.
- Establecer un método para sintetizar otras epidithiodiketopiperazinas complejas.
Principales métodos:
- Estrategia de síntesis total enantioselectiva. estrategia de síntesis total enantioselectiva.
- Reacciones de tetrahidroxilación y tetraciolación en estadio avanzado.
- Introducción leve del núcleo de la epidithiodiketopiperazina.
Principales resultados:
- Se logró con éxito una síntesis total concisa y enantioselectiva de (+) -11,11'-dideoxyverticilina A.
- Se desarrollaron reacciones altamente estereoselectivas y quimioselectivas para las transformaciones clave.
- Se estableció una estrategia de paso final suave para el núcleo sensible de epidithiodiketopiperazina.
Conclusiones:
- Se logró la síntesis total de (+) -11,11'-dideoxyverticillin A, superando un desafío de larga data.
- La estrategia sintética desarrollada, inspirada en la biosíntesis, es efectiva para esta familia de alcaloides.
- Este trabajo abre caminos para la síntesis de otras epidithiodiketopiperazinas diméricas complejas.
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