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Un enfoque conciso y enantioselectivo para la síntesis de alcaloides de yohimbina

Eric R Miller¹, M Todd Hovey¹, Karl A Scheidt¹

¹Department of Chemistry, Center for Molecular Innovation and Drug Discovery , Northwestern University , 2145 Sheridan Road , Evanston , Illinois 60208 , United States.

Journal of the American Chemical Society

|January 18, 2020

Resumen

Los investigadores desarrollaron una nueva síntesis para los alcaloides de yohimbina como la (-) -rawolscina. Este método eficiente utiliza reacciones catalizadas por carbenos heterocíclicos (NHC) para crear estructuras clave para la investigación biomédica.

Área de la Ciencia:

Química orgánica
Química sintética
Química medicinal

Sus antecedentes:

Los alcaloides de yohimbina poseen propiedades farmacológicas significativas.
Las rutas sintéticas existentes pueden ser largas y carecen de control estereoquímico.

Objetivo del estudio:

Desarrollar una síntesis concisa y enantioselectiva de los alcaloides de yohimbina.
Establecer una plataforma versátil para acceder a diversas estructuras alcaloides.

Principales métodos:

Dimerización catalizada por el carbeno N-heterocíclico (NHC).
Secuencia de ciclización de la amidación/ion N-acilíminio.
Síntesis estereoselectiva de las estructuras alcaloides centrales.

Principales resultados:

Se ha sintetizado con éxito (-) -rawolscin y (-) -alloyohimbane.
Construido cuatro de cinco anillos y tres estereocentros en dos pasos.
Proporcionó acceso a los cuatro arreglos diastereoméricos del núcleo estereotriado.

Conclusiones:

La estrategia desarrollada catalizada por NHC ofrece una ruta eficiente a los alcaloides de yohimbina.
Esta plataforma permite la síntesis de varios alcaloides complejos para estudios biomédicos.
El método permite el acceso a ambos enantiómeros de los compuestos objetivo.

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