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Síntesis total de la (-) -ocilactomycin también conocida como (-) -okilactomycin

Amos B Smith¹, Kallol Basu, Todd Bosanac

¹Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu

Journal of the American Chemical Society

|November 14, 2007

Resumen

Se logró una nueva síntesis de (-) -okilactomicina utilizando un enfoque convergente. Los pasos clave involucraron un reordenamiento diastereoselectivo de oxy-Cope y una unión Petasis-Ferrier para una eficiente construcción de macrociclos.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.
Síntesis de Productos Naturales.

Sus antecedentes:

(-) La ocilactomicina es un producto natural complejo con actividades biológicas potenciales.
Las rutas sintéticas eficientes son cruciales para acceder y estudiar tales moléculas.

Objetivo del estudio:

Desarrollar una estrategia sintética altamente convergente y eficiente para la (-) -okilactomicina.
Para mostrar las transformaciones sintéticas clave para la construcción de moléculas complejas.

Principales métodos:

Secuencia de oxidación y reordenamiento de oxy-Cope diastereoselectivo. secuencia de oxidación.
Táctica de unión y reorganización de Petasis y Ferrier.
Metátesis de cierre de anillo (MCR) para la formación de macrociclos.

Principales resultados:

Se ejecutó con éxito una síntesis altamente convergente de (-) -okilactomicina.
El reordenamiento de oxy-Cope a nivel de estrategia proporcionó una excelente diastereoselectividad.
Se empleó una reacción RCM eficiente para construir el núcleo macrocíclico de 13 miembros.

Conclusiones:

La ruta sintética descrita es eficiente y convergente.
Las metodologías empleadas son valiosas para la síntesis de compuestos macrocíclicos complejos.
Esta síntesis proporciona una vía viable hacia la (-) -ocilactomicina.

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