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An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Bronsted acid catalysis cascade.

ABSTRACT: The desymmetrization of p-peroxyquinols using a Brønsted 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.

SUBMITTER: Rubush DM 

PROVIDER: S-EPMC3433808 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

Rubush David M DM   Morges Michelle A MA   Rose Barbara J BJ   Thamm Douglas H DH   Rovis Tomislav T  

Journal of the American Chemical Society 20120807 33

The desymmetrization of p-peroxyquinols using a Brønsted 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. ...[more]

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