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Paper | Regular issue | Vol 38, No. 7, 1994, pp.1497-1506
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6646
Novel Rearrangement of the Trioxane Ring System of the Antimalarial Arteether upon Treatment with Acid in an Aqueous Methanol Solvent System

John K. Baker* and Hsien Tao Chi

*Department of Medicinal Chemistry and the Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, Mississippi 38677, U. S. A.

Abstract

While arteether does not have a uv-chromophore, the treatment of arteether with a HCl, water, methanol system has been previously proposed as a method of generating a uv-chromophore upon which to base a quantitative analysis. The present study demonstrates that the originally proposed structure for the product was not correct and that the reaction is far more complex than originally proposed. It was found that the reaction yields 5 different α,β-unsaturated ketones (A-1, A-2, A-3, A-4, and A-5; whose structures are reported here for the first time) that have strong uv chromophores and 4 additional products (new compounds B-1 and B-2; previously reported α-artemether and β-artemether) that do not have any significant chromophores. The structure and stereochemistry of these novel reaction products were determined using thermospray hplc/ms, 1H-nmr, 13C-nmr, and two-dimensional nmr methods.