Effect of the medium on the pathway of the reaction of S-(1S,2R,3S,5R)-2-formyl-6,6-dimethylnorpinan-3-yl thioacetate with chlorine dioxide

Abstract

The reaction of S-(1S,2R,3S,5R)-2-formyl-6,6-dimethylnorpinan-3-yl thioacetate with chlorine dioxide in a pyridine—water solution was studied. The oxidative cleavage of the C—C bond between the carbonyl carbon and α-carbon atoms of the starting 2-formyl thioacetate of the pinane structure afforded new polyfunctional derivatives, (3S)- and (3R)-2-keto-3-sulfonic acids and 2-keto-3-chloro-3-sulfonic acid. The structure of the latter compound was determined by X-ray diffraction. The antifungal activity of the starting thioacetate and its keto derivative was evaluated against micellar forms of the fungi Aspergillus niger and Fusarium oxysporum and the yeast fungi of the genus Candida.