An Asymmetric Synthesis of 1,2,4-Trioxane Anticancer Agents via Desymmetrization of Peroxyquinols through a Bronsted Acid Catalysis Cascade

作者:Rubush David M; Morges Michelle A; Rose Barbara J; Thamm Douglas H; Rovis Tomislav*
来源:Journal of the American Chemical Society, 2012, 134(33): 13554-13557.
DOI:10.1021/ja3052427

摘要

The desymmetrization of p-peroxyquinols using a Bronsted acid-catalyzed acetalization/oxa-Michael cascade was achieved in high yields and selectivities for a variety of aliphatic and aryl aldehydes. Mechanistic studies, suggest that the reaction proceeds through a dynamic kinetic resolution of the peroxy hemiacetal intermediate. The resulting 1,2,4-trioxane products were derivatized and show potent cancer cell-growth inhibition.

  • 出版日期2012-8-22