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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Una síntesis general de dienamina reductora catalizada por iridio permite una síntesis de cinco pasos de catarantina

Pablo Gabriel¹, Yaseen A Almehmadi^1,2, Zeng Rong Wong¹

¹Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, United Kingdom.

Journal of the American Chemical Society

|July 13, 2021

Resumen

Una nueva estrategia de reducción permite la síntesis estereo y regioselectiva de isoquinuclidinas. Este método utiliza la activación catalizada por iridio de los lactamos para reacciones eficientes de cicloadición, produciendo aminas bicíclicas complejas.

Área de la Ciencia:

Química orgánica
Química sintética
Catálisis

Sus antecedentes:

Las isoquinuclidinas son motivos estructurales importantes en los productos naturales y farmacéuticos.
Desarrollar rutas sintéticas eficientes y estereoselectivas para estos compuestos sigue siendo un desafío.

Objetivo del estudio:

Desarrollar una nueva estrategia de reducción para la síntesis de isoquinucleidas funcionalizadas.
Explorar el alcance y las limitaciones de esta nueva metodología sintética.

Principales métodos:

Activación reductora quimio-selectiva por iridio ((I) de los β,γ-lactamas insaturados.
Los intermediarios de dienamina se someten a reacciones de cicloadición [4 + 2] con varios dienófilos.

Principales resultados:

Se ha logrado la síntesis estereo y regioselectiva de isoquinuclidinas funcionalizadas.
El método se extendió con éxito a los materiales de partida alifáticos, obteniendo productos de ciclohexenamina.
Aplicado como un paso clave en la síntesis total más corta de catarantina hasta la fecha.

Conclusiones:

Se ha establecido una nueva estrategia sintética versátil y eficiente para las isoquinuclidinas.
Este enfoque ofrece una ruta simplificada a aminas y productos naturales complejos.

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