EFFICIENT SYNTHESES FOR OPTICALLY PURE STEREOGENICALLY LABILE 4-SUBSTITUTED-2-HYDROXYTETRONIC ACIDS

The aci-reductone 4-(4-chlorophenyl)-2-hydroxytetronic acid (CHTA, 1) exhibits antilipidemic and antiaggregatory properties that differ from those of classical phenoxyacetic acids.1,2 To further explore enzymatic inhibitory mechanisms of action relevant to the treatment and/or prevention of atherosclerosis, we required methods for the synthesis of optically pure 4-alkyl- and 4-aryl-2-hydroxytetronic acids 2 and 3. The redox functionality present in these species is also found in vitamin C, but outside the scope of vitamin C research this function has received little attention.3 Although, unsubstituted, 2-alkyl-, and 2-acyltetronic acids are frequently found in nature,4,5 the 2-hydroxy-substituted redox system, to our knowledge, is only found in vitamin C and the macrolide antibiotic chlorothricin6. © 1990, American Chemical Society. All rights reserved.