1: 1.) Et3N, trimethylaluminum / 1.) CH2Cl2, RT, 15 min, 2.) CH2Cl2, reflux, 48 h 2: Jones reagent / acetone / 2 h / 0 - 20 °C 3: benzene / 2.5 h / Heating 4: 83 percent / Et4NOTS / methanol / anodic oxidation, carbon rod anode, Pt cathode 5: TiCl4 / CH2Cl2 / 36 h / Ambient temperature 6: 1.) O3, 2.) Zn-dust, HOAc / 1.) MeOH, -78 deg C, 0.5 h, 2.) MeOH, RT, 48 h 7: 38 percent / Et3N / benzene / 0 °C 8: 55 percent / 2,3-dichloro-4,5-dicyanobenzoquinone / dioxane / 3 h / Heating 9: 0.01 N HCl / methanol; H2O / 2 h / 105 °C 10: Bu4NBr, 9 M aq. HBr / 0.75 h / 110 °C View Scheme