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Síntesis total de la hibridafinifilina B
Wenhao Zhang1, Ming Ding1, Jian Li1
1State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
Journal of the American Chemical Society
|March 2, 2018
Resumen
Los investigadores lograron la primera síntesis total de la hibridafinifilina B, un alcaloide complejo de Daphniphyllum. Este avance utilizó una reacción intermolecular Diels-Alder en etapa tardía, avanzando en la química orgánica sintética.
Área de la Ciencia:
- Química orgánica
- Síntesis de productos naturales
- Química medicinal
Sus antecedentes:
- La hibridafinifilina B es un alcaloide complejo de Daphniphyllum con 11 anillos y 19 estereocentros.
- La estructura intrincada de la hibridafinifilina B presenta un desafío significativo para la síntesis total.
Objetivo del estudio:
- Para informar de la primera síntesis total de la hibridafinifilina B.
- Desarrollar una ruta escalable para los intermediarios clave, incluida la daphnilongeranina B.
- Para explorar nuevas estrategias sintéticas, como las reacciones intermoleculares de Diels-Alder en etapa tardía.
Principales métodos:
- Se estableció una ruta escalable hacia la daphnilongeranina B.
- Una reorganización Claisen clave fue optimizada para suprimir la reorganización Cope no deseada.
- La síntesis involucró una reacción intermolecular de Diels-Alder en etapa tardía entre un derivado de ciclopentadieno y tetraacetato de asperulosido.
- Se desarrolló un protocolo de una sola olla para la formación de dieno y la reacción de Diels-Alder.
Principales resultados:
- Se logró con éxito la primera síntesis total de hibridafinifilina B.
- También se sintetizó dafnionina E y deshidrodafinilongeranina B.
- La síntesis demostró la utilidad de una reacción intermolecular de Diels-Alder en etapa tardía en la construcción de marcos alcaloides complejos.
- Un nuevo protocolo de una sola olla simplificó el proceso de formación de dieno y cicloadición.
Conclusiones:
- La síntesis total de la hibridafinifilina B proporciona una valiosa contribución al campo de la síntesis de productos naturales.
- Las estrategias sintéticas desarrolladas ofrecen potencial para acceder a otros alcaloides complejos de Daphniphyllum.
- Este trabajo destaca el poder de las reacciones de Diels-Alder en el ensamblaje de intrincadas arquitecturas moleculares.
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