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Síntesis total asimétrica de (-) -spirocensilida A

Xin-Ting Liang¹, Jia-Hua Chen¹, Zhen Yang^1,2,3

¹Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science, and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China.

Journal of the American Chemical Society

|April 15, 2020

Resumen

Se informa de la primera síntesis total asimétrica de (-) -spirochensilida A. Los pasos clave incluyen la construcción estereoselectiva de centros quaternos quirales y la formación del motivo espiroketal.

Área de la Ciencia:

Química orgánica
Química sintética
Síntesis total

Sus antecedentes:

El (-) -spirocensilido A es un producto natural complejo.
Su estructura única presenta un desafío sintético significativo.

Objetivo del estudio:

Para lograr la primera síntesis total asimétrica de (-) -spirochensilida A.
Desarrollar nuevas metodologías sintéticas para la construcción de arquitecturas moleculares complejas.

Principales métodos:

Construcción estereoselectiva de centros quirales cuaternarios vecinos utilizando un reordenamiento de semipinacol.
Reacción de Pauson-Khand mediada por el tungsteno para la instalación de un centro quiral cuaternario.
Ciclización oxidativa a base de furanos para la formación de espirocetos.

Principales resultados:

Se ha completado con éxito la síntesis total asimétrica de (-) -spirochensilida A.
Demostración de una alta estereoselectividad en las reacciones clave de formación de enlaces.
Instalación eficiente de múltiples centros quirálicos cuaternarios.

Conclusiones:

La vía sintética desarrollada proporciona una vía viable para el (-) -spirochensilida A.
La metodología puede aplicarse a la síntesis de otros productos naturales complejos.
Este trabajo amplía el conjunto de herramientas para la síntesis asimétrica de moléculas con estereocentros cuaternarios.

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