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Síntesis total convergente y enantioselectiva biomimética de (-) -communesin F

Stephen P Lathrop¹, Matthew Pompeo¹, Wen-Tau T Chang¹

¹Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society

|June 1, 2016

Resumen

Los investigadores lograron la primera síntesis biomimética de (-) -communesin F utilizando una nueva etapa de heterodimerización y intercambio aminal. Este método eficiente construye rápidamente el núcleo heptacíclico complejo, ofreciendo una nueva vía para la síntesis de productos naturales.

Área de la Ciencia:

Química orgánica
Química sintética
Síntesis de productos naturales

Sus antecedentes:

La comunesin F es un producto natural complejo con una estructura heptacíclica compleja.
Las rutas sintéticas existentes a menudo son largas y carecen de eficiencia.
Los enfoques biomiméticos pueden ofrecer soluciones más eficientes y elegantes.

Objetivo del estudio:

Desarrollar la primera síntesis total enantioselectiva biomimética de (-) -communesin F.
Establecer una estrategia eficiente y convergente para la construcción del núcleo de las comunas.
Explorar nuevas metodologías sintéticas inspiradas en las vías naturales.

Principales métodos:

Ensamblaje dirigido por diazeno de dos fragmentos avanzados para el enlace C3a-C3a'.
Reorganización aminal inspirada biogenéticamente para la formación de núcleos heptacíclicos.
Las reacciones de halociclinación asimétrica catalítica, oxiaaminación diastereoselectiva y alilación estereoselectiva para la síntesis de fragmentos.

Principales resultados:

Construcción exitosa del enlace congestionado C3a-C3a' en tres pasos.
Formación eficiente de las comunas heptacíclicas en el núcleo en dos pasos adicionales.
Desarrollo de síntesis versátiles y estereocontroladas para fragmentos clave.

Conclusiones:

El método descrito proporciona una síntesis biomimética altamente convergente y eficiente de (-) -communesin F.
La estrategia pone de relieve el poder del ensamblaje en etapa tardía y las transformaciones inspiradas en la biogenética.
Este trabajo ofrece un nuevo enfoque valioso para la síntesis de productos naturales complejos.

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