Synthesis of deuterium labelled analogs of the ubiquinone headgroup

Deuterium labelled analogs of 2,3 ‐ dimethoxy ‐ 5 ‐ methyl ‐ 1,4 ‐ benzoquinone (2,3 ‐ dimethoxy ‐ 5 methyl[2H3] ‐ 1,4 ‐ benzoquinone; 2,3 ‐ dimethyoxy[2H6] ‐ 5 ‐ methyl ‐ 1,4 ‐ benzoquinone; 2,3 ‐ dimethoxy[2H6] ‐ 5 ‐ methyl[2H3] ‐ 1,4 ‐ benzoquinone) were prepared in five steps starting from 3,4,5 ‐ trihydroxybenzoic acid. The proposed synthetic route results in 100% specific labelling and gives good overall yields. Mass spectra of the labelled derivatives will be briefly discussed.