1: NaIO4 / H2O; acetone 2: 1.) Ac2O, (CF3CO)2O, r.t., 48 hr 2.) EtOH, 1N NaOH, r.t., 0.5 hr View Scheme

1: 79 percent / t-BuOOH / V2O5 / ethyl acetate / 48 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) 1 h, -78 deg C to r. t. 3: 73 percent / oxygen, CuCl / PdCl2 / dimethylformamide; H2O / 12 h / Ambient temperature 4: DBU / CH2Cl2 / 1 h / Heating 5: 85 percent / H2SO4 / acetic acid; diethyl ether / 1.5 h / 0 °C View Scheme

1: 79 percent / t-BuOOH / V2O5 / ethyl acetate / 48 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) 1 h, -78 deg C to r. t. 3: 73 percent / oxygen, CuCl / PdCl2 / dimethylformamide; H2O / 12 h / Ambient temperature 4: DBU / CH2Cl2 / 1 h / Heating View Scheme

1: NaIO4 / H2O; acetone 2: Heating; distillative thermolysis View Scheme

1: 88 percent / 30percent H2O2 / dioxane / Ambient temperature 2: 55 percent / (CF3CO)2O / 72 h / Ambient temperature 3: 84 percent / NaBH4 / aq. ethanol / 12 h / Ambient temperature View Scheme

Yield given. Multistep reaction;