Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 33, Pages 13554-13557Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja3052427
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- NIGMS [GM72586]
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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.
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