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Una estrategia unificada para la síntesis de alcaloides de Lycopodium que contienen anillos de siete miembros

Amy S Lee¹, Brian B Liau, Matthew D Shair

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

Journal of the American Chemical Society

|August 26, 2014

Resumen

Los investigadores desarrollaron una nueva estrategia de secuencia en cascada para sintetizar complejos alcaloides de Lycopodium. Este enfoque unificado produce eficientemente compuestos como la (+) -fastigiatina y la (-) -himeradina A, ofreciendo información sobre su biosíntesis.

Área de la Ciencia:

Síntesis de Productos Naturales.
Química orgánica es la química orgánica.
La biosíntesis es la biosíntesis.

Sus antecedentes:

Un grupo único de alcaloides de Lycopodium presenta una subestructura compartida de anillos de 7 miembros.
Estos alcaloides pueden provenir de un precursor biosintético común, lo que sugiere el potencial de estrategias sintéticas unificadas.

Objetivo del estudio:

Desarrollar una estrategia unificada, inspirada en la biosíntesis, para la síntesis de complejos alcaloides policíclicos de licopodio policíclicos.
Para acceder de manera eficiente a los alcaloides que contienen la característica subestructura de anillo de siete miembros utilizando secuencias en cascada.

Principales métodos:

Empleó una estrategia de secuencia en cascada para la síntesis total de alcaloides de Lycopodium.
Desarrolló un método diastereoselectivo de una sola olla para construir el núcleo común de anillo de 7 miembros.
Utilizó reacciones biomiméticas transannulares de Mannich y reducciones de iminas para transformaciones posteriores.

Principales resultados:

Se logró la primera síntesis total de (+) -fastigiatina.
Se ha sintetizado con éxito (-) -himeradina A, (-) -licopecurina, (-) -dehidrolicopecurina, (+) -liconadina A y (-) -liconadina B.
Demostró la eficacia de la estrategia unificada en el acceso a diversos alcaloides de anillo de 7 miembros de Lycopodium.

Conclusiones:

La estrategia de secuencia en cascada desarrollada proporciona un acceso eficiente a una gama de alcaloides de anillo de 7 miembros de Lycopodium.
Este enfoque ofrece valiosos conocimientos sobre los orígenes biosintéticos de estos complejos productos naturales.
La estrategia tiene potencial para sintetizar todos los alcaloides de Lycopodium que poseen el núcleo de anillo de 7 miembros.

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