1: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 2: 94 percent / DIBAL / toluene / 1 h / -78 °C 3: 99 percent / pyridine, DMAP / 0.5 h / 0 °C 4: 1.) n-BuLi, Me3SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h 5: 71 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.5 h / -20 °C 6: 43 percent / BBr3 / CH2Cl2 / 2.5 h / -78 - -10 °C 7: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 8: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating 9: 87 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 10: 77 percent / aq. potassium nitrosodisulfonate, KH2PO4 / acetone / 0.5 h / Ambient temperature View Scheme