Benzylic functionalization of dehydroabietane derivatives as a convenient way to sulfur compounds

For the first time, dehydroabietane-derived alcohols containing an OH group at the C-7 position were used to produce thioacetates by direct ZnCl 2 -catalyzed substitution of the hydroxyl group. Thioacetates obtained were found to give the corresponding disulfides when treated with MeONa in the presence of atmospheric oxygen with no observation of any thiol formation. In addition, the ability of diol with two hydroxyl groups at C-7 and C-18 to be converted to a cyclic dimer was detected. Dehydroabietane derivatives with a sulfur atom at the C-7 position (thiol, disulfides), which are promising for the production of biologically active substances, were first obtained. Graphical abstract