Concise Three Step Synthesis of the Bioactive Alkaloid Huajiaosimuline via a Zn(OTf) 2 ‐Promoted Meinwald Rearrangement

The synthesis of the biologically active alkaloid huajiaosimulne, isolated from the roots of Zanthoxylum simulans, is reported. The natural product was assembled from simple commercial reagents via initial domino Knoevenagel/oxa-6π-electrocyclization followed by epoxidation and an epoxide/ketone rearrangement promoted by Zn(OTf)2. In vitro cytotoxicity assays identified natural products huajiaosimuline and simulansine as moderate antiproliferative agents against murine colon cancer CT26 cells.

Palabras clave: CANCER , ALKALOIDS , ZANTHOXYLUM SIMULANS , PYRANOQUINOLONE

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Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)

Identificadores

URI: http://hdl.handle.net/11336/263388

URL: https://onlinelibrary.wiley.com/doi/10.1002/cbdv.202402680

DOI: http://dx.doi.org/10.1002/cbdv.202402680

Colecciones

Articulos(IQUIFIB)
Articulos de INST.DE QUIMICA Y FISICO-QUIMICA BIOLOGICAS "PROF. ALEJANDRO C. PALADINI"

Articulos(IQUIR)
Articulos de INST.DE QUIMICA ROSARIO

Citación

Adessi Cofré, Tonino Graziano; Centurión, Enzo Federico Gabriel; De La Horra, Camila; Chocan, Camila; Bajicoff, Sofia Veronica; et al.; Concise Three Step Synthesis of the Bioactive Alkaloid Huajiaosimuline via a Zn(OTf) 2 ‐Promoted Meinwald Rearrangement; Wiley VCH Verlag; Chemistry and Biodiversity; 22; 4; 12-2024; 1-8

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