Electrochemical reduction of prostanoid syntone 7α-hydroxy-6Β-3′-oxo-4′-(m-chlorophenoxy)-1′e-butenyl-cis-2-oxabicyclo[3.3.0]octan-3-one

The reactivity of the prostanoid syntone 7α-hydroxy-6Β-3′-oxo-4′-(m-chlorophenoxy)-1′E-butenyl-cis-2-oxabicyclo[3.3.0]octan-3-one is determined by the presence of an enone fragment in the molecule. The electrochemical reduction of this enone in DMF proceeds in two stages. In the first stage the single-electron reduction is accompanied by the dimerization of the originally formed anion radicals. The further reduction of the anion radical is also complicated by the subsequent reactions. The four-stage reduction of the investigated enone in 50% aqueous ethanol reflects the influence of the protogenic medium on its electrochemical behavior. The formation of a diketone at the first and of a saturated ketone at the second stage has been explained by the dimerization of the originally formed anion radical and its further reduction. At the potentials of the third and fourth stages the original diketone is reduced to the corresponding ketoalcohol, which catalyzes the discharge of hydrogen in the potential region of the fourth wave.