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Síntesis total de la (-) -nakadomarina A en su conjunto

Simone Bonazzi¹, Bichu Cheng, Joseph S Wzorek

¹Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.

Journal of the American Chemical Society

|June 12, 2013

Resumen

Los investigadores informan de una nueva síntesis convergente para el alcaloide policíclico (-) -nakadomarin A. Este método eficiente utiliza sintonas lactámicas clave y una reacción en cascada para construir el complejo esqueleto molecular.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.
Síntesis de Productos Naturales.

Sus antecedentes:

La (-) -nadomarina A es un alcaloide policíclico complejo con una estructura molecular compleja.
Las rutas sintéticas anteriores para obtener alcaloides similares han sido largas e ineficientes.

Objetivo del estudio:

Desarrollar una estrategia sintética eficiente y convergente para la (-) -nakadomarina A.
Para establecer una síntesis estereocontrolada utilizando un intermediario clave del lactamo bicíclico.

Principales métodos:

El enfoque de síntesis convergente.
Preparación de dos sintetizadores claves del lactamo: el lactamo macrocíclico 4 (8 pasos) y el biciclo[6.3.0] lactamo 5 (5 pasos).
Reacción en cascada promovida por el triflato de sililo entre los síntonos 4 y 5.

Principales resultados:

El ensamblaje exitoso de la mayoría del esqueleto de (-) -nakadomarin A a través de una reacción en cascada.
La estereoquímica fue controlada por un solo estereocentro en Synthon 5.
La síntesis se completó en un total de 14 pasos, incluida la formación final de bonos.

Conclusiones:

La síntesis reportada representa un avance significativo en la construcción eficiente de alcaloides policíclicos complejos.
La estrategia destaca la utilidad de las reacciones en cascada y los intermediarios estereocontrolados en la síntesis de productos naturales.

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