1: HIO4 / methanol / 1 h / 0 °C 2: NaBH4 / methanol / 1 h / Ambient temperature 3: CF3CO2H / CH2Cl2 / 1.5 h / Ambient temperature 4: H2/PdCl2 / methanol / 1 h View Scheme

periodic acid in methanol T=0°C; 1 h;

1: HIO4 / methanol / 1 h / 0 °C 2: NaBH4 / methanol / 1 h / Ambient temperature 3: CF3CO2H / CH2Cl2 / 1.5 h / Ambient temperature 4: H2/PdCl2 / methanol / 1 h 5: toluene / 2 h / Heating View Scheme

1: HIO4 / methanol / 1 h / 0 °C 2: NaBH4 / methanol / 1 h / Ambient temperature 3: CF3CO2H / CH2Cl2 / 1.5 h / Ambient temperature 4: H2/PdCl2 / methanol / 1 h 5: toluene / 2 h / Heating 6: DMAP / CH2Cl2 / 2 h / Ambient temperature 7: dimethylsulfoxide / 1 h / 90 °C 8: 2N NaOH / ethanol / 3 h / 90 °C View Scheme

1: HIO4 / methanol / 1 h / 0 °C 2: NaBH4 / methanol / 1 h / Ambient temperature 3: CF3CO2H / CH2Cl2 / 1.5 h / Ambient temperature 4: H2/PdCl2 / methanol / 1 h 5: toluene / 2 h / Heating View Scheme

1: HIO4 / methanol / 1 h / 0 °C 2: NaBH4 / methanol / 1 h / Ambient temperature 3: CF3CO2H / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

1: HIO4 / methanol / 1 h / 0 °C 2: NaBH4 / methanol / 1 h / Ambient temperature 3: CF3CO2H / CH2Cl2 / 1.5 h / Ambient temperature 4: H2/PdCl2 / methanol / 1 h 5: toluene / 2 h / Heating View Scheme