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Síntesis Total Estereodivergente en Siete Pasos de Punicafolina y Macaranganina

Hiromitsu Shibayama¹, Yoshihiro Ueda¹, Takashi Tanaka²

¹Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan.

Journal of the American Chemical Society

|January 14, 2021

Resumen

Las primeras síntesis totales de punicafolina y macaranganina se lograron en solo siete pasos a partir de la glucosa. Este método eficiente evita los grupos protectores, lo que permite un rápido acceso a estos complejos glucósidos naturales.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales

Sus antecedentes:

La punicafolina y la macaranganina son glucósidos naturales complejos.
Las síntesis anteriores fueron largas y requirieron grupos protectores.

Objetivo del estudio:

Desarrollar las primeras síntesis totales de punicafolina y macaranganina.
Para lograr estas síntesis de una manera muy eficiente, en pasos cortos.

Principales métodos:

Se utiliza la α-d-glucosa comercial como material de partida.
Se utiliza la galoilación secuencial y selectiva del sitio de la glucosa no protegida.
Se ha logrado una construcción estereodivergente del puente 3,6-HHDP a través del acoplamiento oxidativo del fenol.

Principales resultados:

Con éxito sintetizó punicafolina y macaranganina en siete pasos cada uno.
Se ha demostrado una estrategia de galloilación controlada por catalizador.
Mostró una nueva síntesis estereodivergente del puente HHDP.
Se obtienen síntesis sin necesidad de grupos protectores sobre la glucosa.

Conclusiones:

Estableció las primeras síntesis totales eficientes y en pasos cortos de punicafolina y macaranganina.
Destacó la utilidad de las reacciones controladas por catalizadores y el acoplamiento estereodivergente para la síntesis de productos naturales complejos.

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