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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
Published on: May 27, 2014
Síntesis asimétrica de los ocho estereotetrados de dipropionato de siete átomos de carbono
Ahmad El-Awa1, Xavier Mollat du Jourdin, Philip L Fuchs
1Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
Journal of the American Chemical Society
|June 15, 2007
Resumen
Este estudio detalla un nuevo método para sintetizar estereotetrados, bloques de construcción cruciales para los productos naturales polipropionados. El proceso implica la epoxidación diastereoselectiva y la metilación estereocontrolada, dando como resultado siete de los ocho posibles estereotetrados.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química sintética de la química sintética.
Sus antecedentes:
- Los productos naturales de polipropionato son moléculas complejas con una actividad biológica significativa.
- La síntesis eficiente de estereotratados es esencial para acceder a estos productos naturales.
Objetivo del estudio:
- Desarrollar un método diastereoselectivo para la síntesis de estereotratados.
- Proporcionar acceso a siete de los ocho posibles estereotratados relevantes para la síntesis de productos naturales.
Principales métodos:
- Epoxidación diastereoselectiva de las sulfonas de cicloheptadienilo enantiopuro.
- Sintetización y anti metilación estereocontroladas de las sulfonas de epoxivinilo.
- Cristalografía de rayos X para la confirmación estereoquímica.
Principales resultados:
- Se obtienen altos rendimientos y relaciones diastereoméricas para las sulfonas de epoxivinilo.
- Acceso a los ocho posibles estereotratados, siete de los cuales se encuentran comúnmente en productos naturales.
- Estereotetrados confirmados por cristalografía de rayos X y escisión oxidativa para una mayor síntesis.
Conclusiones:
- El método desarrollado proporciona una ruta versátil a los estereotraders.
- Este enfoque facilita la síntesis de productos naturales complejos de polipropionato.
- Los estereotetrados acíclicos resultantes están preparados para su elaboración en fragmentos moleculares más grandes.
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