sulfuric acid in ethanol 0.5 h; Heating;

selenium(IV) oxide in chloroform T=20°C; Oxidation; 12 h;

1: 87 percent / NaOAc; zinc dust / 0.25 h / Heating 2: 64 percent / K2CO3; Na2S2O4 / H2O; methanol / 96 h / 29 °C 3: 70 percent / K2CO3 / acetone / 6 h / 29 °C 4: 80 percent / NaOH; Na2S2O4 / methanol; H2O / 24 h / 20 °C 5: 60 percent / K2CO3 / acetone / 12 h / 29 °C 6: HBF4*Et2O / CH2Cl2 / 0.03 h / 0 - 5 °C 7: 0.026 g / SeO2 / CHCl3 / 12 h / 20 °C View Scheme

1: 64 percent / K2CO3; Na2S2O4 / H2O; methanol / 96 h / 29 °C 2: 70 percent / K2CO3 / acetone / 6 h / 29 °C 3: 80 percent / NaOH; Na2S2O4 / methanol; H2O / 24 h / 20 °C 4: 60 percent / K2CO3 / acetone / 12 h / 29 °C 5: HBF4*Et2O / CH2Cl2 / 0.03 h / 0 - 5 °C 6: 0.026 g / SeO2 / CHCl3 / 12 h / 20 °C View Scheme

1: 70 percent / K2CO3 / acetone / 6 h / 29 °C 2: 80 percent / NaOH; Na2S2O4 / methanol; H2O / 24 h / 20 °C 3: 60 percent / K2CO3 / acetone / 12 h / 29 °C 4: HBF4*Et2O / CH2Cl2 / 0.03 h / 0 - 5 °C 5: 0.026 g / SeO2 / CHCl3 / 12 h / 20 °C View Scheme

1: 60 percent / K2CO3 / acetone / 12 h / 29 °C 2: HBF4*Et2O / CH2Cl2 / 0.03 h / 0 - 5 °C 3: 0.026 g / SeO2 / CHCl3 / 12 h / 20 °C View Scheme

1: 80 percent / NaOH; Na2S2O4 / methanol; H2O / 24 h / 20 °C 2: 60 percent / K2CO3 / acetone / 12 h / 29 °C 3: HBF4*Et2O / CH2Cl2 / 0.03 h / 0 - 5 °C 4: 0.026 g / SeO2 / CHCl3 / 12 h / 20 °C View Scheme

1: HBF4*Et2O / CH2Cl2 / 0.03 h / 0 - 5 °C 2: 0.026 g / SeO2 / CHCl3 / 12 h / 20 °C View Scheme

1: 86 percent / Br2, AcOH / Ambient temperature 2: 1.) NaOMe / 1.) DMSO, RT, 10 min, 2.) DMSO, 6 h 3: 88 percent / p-TsOH / benzene / 72 h / Heating 4: 61 percent / BuLi / tetrahydrofuran; hexane; diethyl ether / 2.5 h / -78 - 20 °C 5: 98 percent / Fe2(CO)9 / benzene / 4 h / Heating 6: 100 percent / 2 M aq. HClO4 / CH2Cl2 / 5 h / Ambient temperature 7: 75 percent / diethyl ether / 0.25 h / Ambient temperature 8: 15 percent / AgO, 6 M aq. HNO3 / dioxane / 0.25 h / Ambient temperature 9: 56 percent / H2SO4 / ethanol / 0.5 h / Heating View Scheme

1: 98 percent / Fe2(CO)9 / benzene / 4 h / Heating 2: 100 percent / 2 M aq. HClO4 / CH2Cl2 / 5 h / Ambient temperature 3: 75 percent / diethyl ether / 0.25 h / Ambient temperature 4: 15 percent / AgO, 6 M aq. HNO3 / dioxane / 0.25 h / Ambient temperature 5: 56 percent / H2SO4 / ethanol / 0.5 h / Heating View Scheme