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Síntesis estereo controlada de la (-) -macrolactina A
Joseph P Marino1, Michael S McClure, David P Holub
1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Journal of the American Chemical Society
|February 21, 2002
Resumen
La síntesis total de (-) -macrolactina A, un macrolido complejo, se logró utilizando nuevos métodos para la introducción de centros estereogénicos. Las etapas clave incluyeron la reducción asimétrica, la química quiral del sulfóxido y técnicas específicas de olefinación.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química sintética de la química sintética.
- Síntesis de Productos Naturales.
Sus antecedentes:
- (-) -Macrolactina A es un macrolido de 24 miembros con una relevancia biológica significativa.
- La síntesis total de macrólidos complejos presenta desafíos estereoquímicos sustanciales.
- Las rutas sintéticas anteriores pueden carecer de eficiencia o estereoselectividad.
Objetivo del estudio:
- Para lograr la primera síntesis total de (-) -macrolactina A.
- Desarrollar y aplicar nuevas metodologías sintéticas para la construcción del núcleo macrolido.
- Introducir dos centros estereogénicos clave de manera eficiente utilizando un nuevo sintetón de 1,3-diol.
Principales métodos:
- Desarrollo de una nueva síntesis de 1,3-diol.
- Reducción asimétrica secuencial de Noyori y metodología de sulfóxido quiral.
- Organometálicos de cuprato derivados del telurio para la instalación de C8 Z/E-dieno.
- La olefinación Julia-Lythgoe para la construcción del segmento C15 E/E.
- La lactonización Yamaguchi para la formación de macrociclos.
Principales resultados:
- El éxito de la síntesis total de (-) -macrolactina A.
- Introducción eficiente de dos centros estereogénicos a través de la síntesis de 1,3-diol.
- Instalación altamente estereoselectiva del dieno C8 y el segmento C15.
- Estrategia de síntesis convergente empleada.
Conclusiones:
- La estrategia sintética desarrollada proporciona una ruta efectiva hacia la (-) -macrolactina A.
- El nuevo sintón de 1,3-diol es una herramienta valiosa para la introducción de centros estereogénicos.
- La síntesis pone de relieve el poder de las reacciones organometálicas y olefinación modernas en la construcción de moléculas complejas.
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