Synthesis of Novel Chiral 18-Sulfanyl and Sulfonyl Dehydroabietane Derivatives

For the first time, dehydroabietic acid ethyl ester was used as initial material to produce the corresponding at the C-18 position thioacetate, thiol, disulfide, sulfonic acid and sulfonyl chloride which open up prospects for the synthesis of other polyfunctional compounds combining a biologically active dehydroabietane fragment with various pharmacophore groups. The optimal conditions were found to directly oxidize dehydroabietanthiol to sulfochloride using chlorine dioxide as an oxidant in the presence of vanadyl acetylacetonate as a catalyst. This sulfochloride synthesized was proposed to use for obtaining a series of sulfonamides with alkyl, aryl, hetaryl and monosaccharide fragments.