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Una síntesis total altamente convergente y biomimética de Portentol
1Department of Chemistry and Center for Integrated Protein Science, Ludwig-Maximilians-Universität München , Butenandtstrasse 5-13, 81377 München, Germany.
Journal of the American Chemical Society
|October 17, 2015
Resumen
Los investigadores informan de una síntesis total eficiente del inusual policetido portentol. Las etapas clave incluyeron reacciones de aldol de boro y una cascada de ciclización biomimética, produciendo portentol y anhidroportentol.
Área de la Ciencia:
- Química orgánica
- Síntesis de productos naturales
- Química de las policetidas
Sus antecedentes:
- El portentol es un policetídeo inusual con una estructura compleja.
- La síntesis de policetidas presenta desafíos significativos debido a su complejidad estereoquímica.
Objetivo del estudio:
- Desarrollar una síntesis total eficiente del producto natural portentol.
- Explorar estrategias biomiméticas para la construcción del núcleo poliquetídeo.
Principales métodos:
- Utilizó tres reacciones de aldol de boro para construir la columna vertebral de carbono lineal.
- Se empleó una cascada de doble ciclización biomimética iniciada por la oxidación.
- Logró la síntesis de portentol y su producto de deshidratación, anhidroportentol.
Principales resultados:
- Ha sintetizado con éxito el portentol, un inusual policetido.
- La síntesis incluyó la construcción de dos estereotriadas anti-anti desafiantes.
- Una cascada biomimética produjo eficientemente tanto el portentol como el anhidroportentol.
Conclusiones:
- La síntesis reportada proporciona una ruta eficiente hacia el portentol.
- El estudio analiza la biosíntesis del portentol y la relevancia del paso sintético clave para las vías biosintéticas.
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