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Síntesis total concisa de las Herculinas B y C

Chi He¹, Thomas P Stratton¹, Phil S Baran¹

¹Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.

Journal of the American Chemical Society

|December 22, 2018

Resumen

Los investigadores informan de una síntesis total directa de las herculinas B y C, imitando su biosíntesis reductora natural. Este estudio ofrece nuevas estrategias para sintetizar estos alcaloides complejos y métodos de reducción suave para las ditopiperazinas.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales
Química medicinal

Sus antecedentes:

Las herculinas B y C son alcaloides complejos con actividades biológicas potenciales.
Estudios previos han aclarado su vía de biosíntesis reductiva.
La síntesis de alcaloides tensados como las herculinas presenta desafíos químicos significativos.

Objetivo del estudio:

Desarrollar una síntesis total sencilla y eficiente de las herculinas B y C.
Modelar la estrategia sintética en la vía biosintética reductora conocida.
Obtener conocimientos estratégicos sobre la síntesis de alcaloides tensados y explorar nuevas metodologías de reducción.

Principales métodos:

La síntesis total comienza con el aminoácido tirosina.
Los pasos clave incluyeron la dimerización, la macrociclización y cuatro reacciones de reducción secuenciales.
Se utilizaron condiciones suaves para la reducción exhaustiva de los intermediarios de la ditopiperazina.

Principales resultados:

Se logró una síntesis total exitosa y simple de las herculinas B y C.
La vía sintética imita efectivamente la biosíntesis reductora propuesta.
Se han desarrollado condiciones suaves y eficientes para reducir las diketopiperazinas.

Conclusiones:

La síntesis reportada proporciona una ruta viable a las herculinas B y C.
El estudio ofrece información estratégica valiosa para la construcción de otros alcaloides tensados.
Las condiciones de reducción desarrolladas son ampliamente aplicables a los derivados de la ditopiperazina.

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