1: 76 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C 2: 84 percent / HCl / diethyl ether / 48 h / Heating 3: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h 4: 64 percent / aq. HCl / tetrahydrofuran / 0.5 h / 40 °C 6: 24 percent / electrochemical oxidation View Scheme

1: 76 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C 2: 84 percent / HCl / diethyl ether / 48 h / Heating 3: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h 4: 54 percent / Ac2O / 48 h / Ambient temperature 5: 82 percent / aq. NaOH / CH2Cl2; methanol / 1 h / Ambient temperature 6: 1.) NaH / 1.) THF, room temperature - 30 min, reflux - 15 min, 2.) THF, room temperature, 20 h 7: 100 percent / aq. NaOH / 24 h / Heating 8: ceric ammonium sulfate 9: NH3 View Scheme