1: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, MeOH, -10 deg C, 45 min, 2.) room temperature, 2 h 2: 47 percent / NaHCO3 / aq. ethanol / 5 h / Heating 3: 87 percent / imidazole, PPh3, I2 / CH2Cl2 / 1.5 h / Ambient temperature 4: 77 percent / Zn, NiCl2*6H2O, I2 / pyridine / 0.75 h / Ambient temperature 5: 82 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) room temperature, 3 h View Scheme

1: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, MeOH, -10 deg C, 45 min, 2.) room temperature, 2 h 2: 47 percent / NaHCO3 / aq. ethanol / 5 h / Heating 3: 87 percent / imidazole, PPh3, I2 / CH2Cl2 / 1.5 h / Ambient temperature 4: 77 percent / Zn, NiCl2*6H2O, I2 / pyridine / 0.75 h / Ambient temperature 5: 82 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) room temperature, 3 h 6: 93 percent / 9-acetylanthracene / methanol / 2 h / 5 °C / Irradiation 7: 71 percent / n-BuNF / tetrahydrofuran / 4 h / 45 °C View Scheme

1: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, MeOH, -10 deg C, 45 min, 2.) room temperature, 2 h 2: 47 percent / NaHCO3 / aq. ethanol / 5 h / Heating 3: 87 percent / imidazole, PPh3, I2 / CH2Cl2 / 1.5 h / Ambient temperature 4: 77 percent / Zn, NiCl2*6H2O, I2 / pyridine / 0.75 h / Ambient temperature 5: 82 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) room temperature, 3 h 6: 81 percent / n-Bu4NF / tetrahydrofuran / 5.5 h / Heating View Scheme