1: 1.) n-BuLi / 1) hexane, Et2O, -78 deg C, 4 h; 2) Et2O, hexane, -85 deg C, 2 h 2: 1.) n-BuLi / 1) hexane, Et2O, -78 deg C, 15 min; 2) hexane, Et2O, 3 h 3: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 48 h / Heating 4: 99 percent / pyridinium dichromate, pyridinium p-toluenesulfonate / CH2Cl2 / 3 h / Ambient temperature 5: 1.) PhLi / 1) cyclohexane, Et2O, THF, -78 deg C, 1 h; 2) cyclohexane, Et2O, THF, -78 deg C, 3 h, -30 deg C, 1 h 6: 1.) CuCN, LiCl / 1) THF, -78 deg C, 15 min; 2) THF, -78 deg C, 10 h, -78 deg C --> rt, 12 h 7: 1.) tetrabutylammonium fluoride, 2.) AG50 WX4 resin / 1) THF, , 12 h, rt; 2) MeOH, rt, 5 h View Scheme

Multi-step reaction with 2 steps 1.1: imidazole / dimethylformamide / 48 h / 60 °C1.2: 96 percent / HCl / tetrahydrofuran / 1 h / 20 °C2.1: 1.79 g / (diacetoxyiodo)benzene; 2,2,6,6-tetramethylpiperidinooxyl radical / CH2Cl2 / 5 h