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

Journal of the American Chemical Society (2012-08-09)
David M Rubush, Michelle A Morges, Barbara J Rose, Douglas H Thamm, Tomislav Rovis
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
8-Hydroxyquinoline, crystalline
Sigma-Aldrich
8-Hydroxyquinoline, ACS reagent, 99%
Sigma-Aldrich
8-Quinolinol hemisulfate salt, ≥98.0% (dry substance, T), yellow
Sigma-Aldrich
8-Quinolinol, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99% (perchloric acid titration)
Supelco
8-Quinolinol, PESTANAL®, analytical standard