hydrogen; platinum(IV) oxide in methanol T=40°C; P=2574.3 Torr;

1: 58 percent / NBS, benzoyl peroxide, / CCl4 / 3 h / Heating 2: 85 percent / dimethylformamide / 2 h / 80 - 90 °C 3: 96 percent / 30percent NaOH, / methanol / 1.5 h / Heating 4: 98 percent / H2, / PtO2, / methanol / 40 °C / 2574.3 Torr View Scheme

1: 85 percent / dimethylformamide / 2 h / 80 - 90 °C 2: 96 percent / 30percent NaOH, / methanol / 1.5 h / Heating 3: 98 percent / H2, / PtO2, / methanol / 40 °C / 2574.3 Torr View Scheme

1: 96 percent / 30percent NaOH, / methanol / 1.5 h / Heating 2: 98 percent / H2, / PtO2, / methanol / 40 °C / 2574.3 Torr View Scheme

1: 1.) NaH, 2.) n-BuLi, / 1.) THF, 70 to 75 deg C, 2 h, 2.) THF, hexane, -70 deg C, 30 min, 3.) THF, hexane, 5 to 10 deg C, overnight, 2: 1.) SOCl2, 2.) K2CO3, / 1.) CH2Cl2, 0 to 10 deg C, 1.5 h, 2.) DMF, RT; 18 h, 3: 60 percent / 80percent m-CPBA, / CH2Cl2 / 0.5 h View Scheme