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Síntesis total de (-) mitreforona A
Matthieu J R Richter1, Michael Schneider1, Marco Brandstätter1
1ETH Zürich , Vladimir-Prelog-Weg 3, HCI , 8093 Zürich , Switzerland.
Journal of the American Chemical Society
|November 10, 2018
Resumen
Los investigadores informan de la primera síntesis de (-) -mitreforona A, un diterpenoide complejo. El estudio detalla nuevas estrategias para construir su anillo único de oxetano incrustado, un reto clave en la síntesis de productos naturales.
Área de la Ciencia:
- Química orgánica
- Síntesis de productos naturales
- Química de los diterpenoides
Sus antecedentes:
- (-) La mitreforona A es un diterpenoide hexacíclico complejo.
- Cuenta con un raro anillo de oxetano esterilizado incrustado.
- La síntesis de tales sistemas de anillos tensados presenta desafíos significativos.
Objetivo del estudio:
- Para lograr la primera síntesis total de (-) -mitreforona A.
- Explorar y evaluar diferentes estrategias sintéticas para la construcción de la fracción de oxetano.
- Desarrollar una ruta eficiente para ensamblar el marco diterpenoide congestionado.
Principales métodos:
- Utilizó tres reacciones de cicloadición [4 + 2] para la construcción rápida de carbociclos.
- Se han investigado las fotocicloadiciones de carbonilo-olefina, las ciclizaciones de tipo Prins y los cierres de anillos oxidativos para la formación de oxetano.
- Desarrolló un nuevo ciclo oxidativo en etapa tardía utilizando el reactivo de Koser.
Principales resultados:
- Se ha sintetizado con éxito (-) -mitreforona A.
- La ruta desarrollada construyó eficientemente el núcleo diterpenoide hexacíclico.
- Se estableció un nuevo método para instalar el oxetano incrustado.
Conclusiones:
- Se logró la primera síntesis total de (-) -mitreforona A.
- El estudio destaca la utilidad de las reacciones de Diels-Alder y la ciclización oxidativa en etapa tardía en la síntesis de moléculas complejas.
- Este trabajo proporciona un valioso modelo sintético para diterpenos relacionados.
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