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Síntesis total de Herquline B y C
Joshua B Cox1, Aoi Kimishima1, John L Wood1
1Department of Chemistry and Biochemistry , Baylor University , One Bear Place 97348 , Waco , Texas 76798 , United States.
Journal of the American Chemical Society
|December 19, 2018
Resumen
Se logró la síntesis total de (-) -herculina B y (+) -herculina C, productos naturales complejos. Una reducción clave de la oxazolina permitió una construcción eficiente del anillo de piperazina en estas síntesis de múltiples pasos.
Área de la Ciencia:
- Química orgánica
- Síntesis de productos naturales
Sus antecedentes:
- (-) Herqulina B es un producto natural con actividad biológica potencial.
- La aclaración estructural de los compuestos relacionados está en curso.
Objetivo del estudio:
- Para describir la síntesis total de la (-) -herculina B.
- Informar sobre la primera síntesis de un congénero recién identificado, la (+) -herculina C.
Principales métodos:
- Síntesis orgánica en varios pasos.
- El paso clave implica la reducción de la oxazolina para la formación del núcleo de la piperazina.
Principales resultados:
- Se ha logrado la síntesis total de (-) -herculina B en 14 pasos.
- Síntesis por primera vez de (+) -herculina C en 13 pasos.
- Se ha demostrado una reducción estratégica de la oxazolina para la construcción de la piperazina.
Conclusiones:
- Las vías sintéticas descritas proporcionan acceso a los alcaloides de herculina.
- El paso clave de reducción es crucial para la formación eficiente de anillos de piperazina.
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