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Síntesis total de la vineomicina B2 en su conjunto

Shunichi Kusumi¹, Satoshi Tomono, Shunsuke Okuzawa

¹Department of Applied Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

Journal of the American Chemical Society

|October 1, 2013

Resumen

Los investigadores lograron la primera síntesis total de vineomicina B2. Los pasos clave incluyeron la nueva C-glucosilación y la quimioselectiva O-glucosilación, lo que permitió la construcción de esta compleja molécula.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.
La glucoquímica es la química de la glucosa.

Sus antecedentes:

La vineomicina B2 es un producto natural complejo con un potencial significado biológico.
Los esfuerzos sintéticos anteriores no han logrado la síntesis total de vineomicina B2.

Objetivo del estudio:

Para lograr la primera síntesis total de vineomicina B2.
Desarrollar nuevas estrategias de glicosilación para la síntesis de moléculas complejas.

Principales métodos:

Síntesis total de la vineomicina B2.
C-glicosilación utilizando un azúcar no protegido.
O-glicosilación quimioselectiva utilizando un azúcar 2,3-insaturado.
Glicosilación controlada por concentración para la introducción simultánea de glicones.

Principales resultados:

Finalización exitosa de la primera síntesis total de vineomicina B2.
Desarrollo de métodos eficientes de C-glucosilación y O-glucosilación.
Demostración de la efectiva introducción simultánea de dos fracciones de glicona.

Conclusiones:

La vía sintética desarrollada proporciona una vía viable a la vineomicina B2.
Las nuevas estrategias de glicosilación son aplicables a la síntesis de otros glucoconjugados complejos.
Este trabajo representa un avance significativo en el campo de la síntesis de productos naturales.

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