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Síntesis total del molanol A

Yuran Wang¹, Rong Zhao¹, Ming Yang¹

¹State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, Gansu Province 730000, China.

Journal of the American Chemical Society

|August 10, 2022

Resumen

Los investigadores lograron la primera síntesis total de molanol A, un grayanoide único con potencial terapéutico para la enfermedad inflamatoria intestinal. Esta síntesis de 15 pasos utilizó una estrategia convergente y reacciones clave de ciclización.

Área de la Ciencia:

Síntesis de productos naturales
Química medicinal
Química orgánica

Sus antecedentes:

Mollanol A, un nuevo grayanoide de tipo molano, presenta un esqueleto único de C-nor-D-homograyanano y un 5,8-epoxido.
Mollanol A exhibe activación transcripcional de promotores de Xbp1, lo que sugiere un potencial terapéutico para la enfermedad inflamatoria intestinal.

Objetivo del estudio:

Se informará de la primera síntesis total de molanol A.
Establecer una ruta sintética para explorar las aplicaciones terapéuticas del molanol A.

Principales métodos:

Se empleó una estrategia de síntesis convergente de 15 pasos.
Las reacciones clave incluyeron una ciclización de Conia-ene catalizada por InCl3 para formar la fracción de biciclo[3.2.1]octano.
Una reacción viníloga de aldol seguida de adición intramolecular de oxa-Michael rápidamente ensambló el núcleo de oxa-biciclo.

Principales resultados:

Finalización con éxito de la primera síntesis total de molanol A.
La síntesis se logró a partir de materiales de partida disponibles en el mercado.

Conclusiones:

La síntesis total de molanol A permite el acceso a este producto natural único.
Este logro sintético permite una mayor investigación de su potencial como agente terapéutico para la enfermedad inflamatoria intestinal.

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