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Reacciones de adición cíclica indólica de los intermediarios catiónicos aza-oxiallilo: Acceso modular a las

Arjun Acharya¹, Devendar Anumandla¹, Christopher S Jeffrey¹

¹Department of Chemistry, University of Nevada , Reno, Nevada 89557-0216, United States.

Journal of the American Chemical Society

|November 13, 2015

Resumen

Una nueva reacción de adición cíclica de aza- 3 + 2 permite una síntesis eficiente de pirroloindolinas funcionalizadas a partir de indoles. Este método fue utilizado para sintetizar el producto natural fisostigmina.

Área de la Ciencia:

Química orgánica
Química sintética

Sus antecedentes:

Las pirroloindolinas son estructuras centrales en numerosos productos naturales y farmacéuticos bioactivos.
El desarrollo de rutas sintéticas eficientes para las pirroloindolinas funcionalizadas es crucial para el descubrimiento de fármacos.

Objetivo del estudio:

Desarrollar una nueva reacción de adición cíclica regioselectiva de aza-3 + 2.
Proporcionar una ruta sintética concisa para las pirroloindolinas altamente funcionales.
Demostrar la utilidad de este método mediante la síntesis de fisostigmina.

Principales métodos:

Reacción de adición cíclica de aza-(3 + 2) de desaromatización regioselectiva.
Se utilizan indoles sustituidos y α-halohidroxamatos como materias primas.
Síntesis concisa del producto natural fisostigmina.

Principales resultados:

Se ha desarrollado con éxito una nueva reacción de cicloadición.
Se logró un acceso rápido a las pirroloindolinas altamente funcionales.
Demostró la síntesis de la fisostigmina utilizando esta nueva metodología.

Conclusiones:

La cicloadición desarrollada aza- 3 + 2 es un método eficaz para sintetizar andamios de pirroloindolina.
Esta transformación ofrece una herramienta valiosa para acceder a moléculas bioactivas complejas.
La síntesis de la fisostigmina pone de relieve la aplicabilidad práctica de esta reacción.

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