1: 100 percent / H2 / Pd/C / CHCl3 2: 96 percent / H2O2; CF3COOH / 25 °C 3: 98 percent / Otera's catalyst / toluene / 120 °C 4: 96 percent / H2 / Pd/C / methanol View Scheme

1: 98 percent / Otera's catalyst / toluene / 120 °C 2: 96 percent / H2 / Pd/C / methanol View Scheme

1: 86 percent / Et3N / Pd(PPh3)2Cl2 / acetonitrile / 25 °C 2: 100 percent / H2 / Pd/C / CHCl3 3: 96 percent / H2O2; CF3COOH / 25 °C 4: 98 percent / Otera's catalyst / toluene / 120 °C 5: 96 percent / H2 / Pd/C / methanol View Scheme

1: 1.) LDA / 1.) THF, hexane, -45 deg C, 1.5 h, 2.) THF, hexane, -45 deg C, 4.5 h 2: 1.) Et3N, trimethylaluminum / 1.) CH2Cl2, RT, 15 min, 2.) CH2Cl2, reflux, 48 h 3: Jones reagent / acetone / 2 h / 0 - 20 °C 4: benzene / 2.5 h / Heating 5: 83 percent / Et4NOTS / methanol / anodic oxidation, carbon rod anode, Pt cathode 6: TiCl4 / CH2Cl2 / 36 h / Ambient temperature 7: 1.) O3, 2.) Zn-dust, HOAc / 1.) MeOH, -78 deg C, 0.5 h, 2.) MeOH, RT, 48 h 8: 38 percent / Et3N / benzene / 0 °C 9: 55 percent / 2,3-dichloro-4,5-dicyanobenzoquinone / dioxane / 3 h / Heating 10: 0.01 N HCl / methanol; H2O / 2 h / 105 °C 11: Bu4NBr, 9 M aq. HBr / 0.75 h / 110 °C View Scheme

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

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

1: TiCl4 / CH2Cl2 / 36 h / Ambient temperature 2: 1.) O3, 2.) Zn-dust, HOAc / 1.) MeOH, -78 deg C, 0.5 h, 2.) MeOH, RT, 48 h 3: 38 percent / Et3N / benzene / 0 °C 4: 55 percent / 2,3-dichloro-4,5-dicyanobenzoquinone / dioxane / 3 h / Heating 5: 0.01 N HCl / methanol; H2O / 2 h / 105 °C 6: Bu4NBr, 9 M aq. HBr / 0.75 h / 110 °C View Scheme

1: 38 percent / Et3N / benzene / 0 °C 2: 55 percent / 2,3-dichloro-4,5-dicyanobenzoquinone / dioxane / 3 h / Heating 3: 0.01 N HCl / methanol; H2O / 2 h / 105 °C 4: Bu4NBr, 9 M aq. HBr / 0.75 h / 110 °C View Scheme

1: 1.) O3, 2.) Zn-dust, HOAc / 1.) MeOH, -78 deg C, 0.5 h, 2.) MeOH, RT, 48 h 2: 38 percent / Et3N / benzene / 0 °C 3: 55 percent / 2,3-dichloro-4,5-dicyanobenzoquinone / dioxane / 3 h / Heating 4: 0.01 N HCl / methanol; H2O / 2 h / 105 °C 5: Bu4NBr, 9 M aq. HBr / 0.75 h / 110 °C View Scheme

1: 55 percent / 2,3-dichloro-4,5-dicyanobenzoquinone / dioxane / 3 h / Heating 2: 0.01 N HCl / methanol; H2O / 2 h / 105 °C 3: Bu4NBr, 9 M aq. HBr / 0.75 h / 110 °C View Scheme