ELECTROCHEMICAL OXIDATION OF METHYL ABIET ATE

Electrochemical oxidation of methyl abietate (1) was investigated unde r some conditions in detail. As the results, two kinds of new compound s methyl 7alpha-acetoxy-13 (beta and alpha)-hydroxy-8(14)-abieten-18-o ate[(2) and (3)] identified by the spectroscopic (UV, MS, IR, NMR) dat a were obtained selectively up to 86% yield by the electrochemical oxi dation of 1 (2 mmol) with an AcOH (30 ml)-H2O(5 ml)-Et3 N(2 g)-carbon electrodes system (constant current density 4 mA/cm2, electricity 4 F/ mol, temperature 18-degrees-C) in an undivided cell. Furthermore, new compounds methyl 7alpha, 13(beta and alpha)-dihydroxy-8(14)-abieten-18 -oate[(2') and (3')] obtained by the alkali hydrolysis of acetoxyl gro up of 2 and 3 were also identified. A possible reaction pathway for th e formation of 2 and 3 is described, too.