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Síntesis total asimétrica y implicaciones biosintéticas de las perovskonas, hidrangenona y hidrangenona B

Baochao Yang¹, Guoen Wen¹, Quan Zhang¹

¹Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering East China Normal University, 3663N Zhongshan Road, Shanghai 200062, China.

Journal of the American Chemical Society

|April 22, 2021

Resumen

Este estudio informa de la primera síntesis total de triterpenoides complejos, perovskonas e hidrangenonas, de las plantas de Salvia. Los hallazgos proporcionan información sobre su biosíntesis y sus posibles aplicaciones medicinales.

Área de la Ciencia:

Síntesis de productos naturales
Química orgánica
Química medicinal

Sus antecedentes:

Las perovskonas y las hidrangenonas son triterpenoides complejos de las plantas de Salvia.
Estos compuestos presentan actividades biológicas significativas, incluidos los efectos antitumorales y antiplasmódicos.

Objetivo del estudio:

Para lograr la síntesis total colectiva de las perovskonas C, D, F, hidrangenona y hidrangenona B.
Para aclarar las posibles vías de biosíntesis de estos productos naturales.

Principales métodos:

Desarrollo de una reacción asimétrica de fotoenolización/Diels-Alder para la construcción del esqueleto de icetexano.
Aplicación de una reacción de Diels-Alder bioinspirada para la síntesis estereospecífica de perovskona.
Utilizando oxidaciones en etapa tardía y reacciones de formación de anillos para el ensamblaje del producto final.

Principales resultados:

El éxito de la síntesis colectiva total de seis triterpenoides objetivo.
Identificación de la perovskatona D como precursor biosintético potencial
Propuso un mecanismo que involucra la escisión oxidativa del anillo y la regeneración para la biosíntesis de hidrangenona.

Conclusiones:

Las estrategias sintéticas proporcionan acceso a valiosos compuestos de perovskona e hidrangenona.
El estudio ofrece información crucial sobre la biosíntesis de estos productos naturales de importancia médica.
Este trabajo sienta las bases para una mayor exploración de los compuestos derivados de la Salvia.

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