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Síntesis enantioselectiva de (-) codeína y (-) morfina

Barry M Trost¹, Weiping Tang

¹Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu

Journal of the American Chemical Society

|December 6, 2002

Resumen

Una nueva estrategia sintética permite la síntesis eficiente de opiáceos y alcaloides de las amarillidas. Este enfoque utiliza reacciones catalizadas por paladio y fotoquímica de luz visible para construir complejas arquitecturas moleculares.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.
Química medicinal Química medicinal es el campo de la química medicinal.

Sus antecedentes:

Los alcaloides opiáceos y de las Amaryllidaceae son productos naturales complejos con propiedades farmacológicas significativas.
Las rutas sintéticas existentes a menudo implican numerosos pasos y un control estereoquímico desafiante.

Objetivo del estudio:

Desarrollar una estrategia sintética novedosa y eficiente para los alcaloides de opiáceos y Amaryllidaceae.
Para establecer un control estereocímico temprano en la síntesis utilizando catálisis asimétrica.

Principales métodos:

Alquilación alilica asimétrica catalizada por paladio para el control estereoquímico.
Vinilación Heck para la construcción del cuarto anillo de codeína/morfina.
La hidroaminación promovida por la luz visible para la formación del anillo final.

Principales resultados:

Se sintetizó un intermediario tricíclico fundamental en seis pasos.
(-) La galantamina se obtuvo en dos pasos adicionales desde el intermediario.
La codeína y la morfina fueron sintetizadas, con la morfina obtenida a través de la desmetilación de alto rendimiento.

Conclusiones:

La estrategia desarrollada proporciona una ruta eficiente a los valiosos productos naturales alcaloides.
La metodología muestra la utilidad de los métodos catalíticos modernos en la síntesis de moléculas complejas.

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