1: LiAlH4 / diethyl ether / 0.33 h / 0 °C 2: ZnBr2, Me3SiBr / CH2Cl2 / 0.5 h / -10 °C 3: 1.) Mg, 2.) Li2CuCl4 / 1.) THF, -60 deg C, 2.) THF, from -60 to 25 deg C, 1 h 4: 98 percent / dimethylaminopyridine (DMAP), pyridine / 0.5 h / 25 °C View Scheme

1: LiAlH4 / diethyl ether / 0.33 h / 0 °C 2: ZnBr2, Me3SiBr / CH2Cl2 / 0.5 h / -10 °C 3: 1.) Mg, 2.) Li2CuCl4 / 1.) THF, -60 deg C, 2.) THF, from -60 to 25 deg C, 1 h View Scheme

1: LiAlH4 / diethyl ether / 0.33 h / 0 °C 2: ZnBr2, Me3SiBr / CH2Cl2 / 0.5 h / -10 °C 3: 100 percent / pyridinium p-toluenesulfonate (PPTS) / CH2Cl2 / 2 h / 25 °C 4: 90 percent / dimethylformamide / 3 h / 60 °C 5: 1.) n-BuLi, HMPA / 1.) THF, hexane, -15 deg C, 30 min, 2.) THF, hexane, -10 deg C, 30 min 6: dimethylaminopyridine (DMAP) / tetrahydrofuran / 0.83 h / -10 - 25 °C 7: NaOH / diethyl ether; methanol / 0.42 h / 25 °C 8: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / Heating 9: 92 percent / pyridinium p-toluenesulfonate (PPTS) / methanol / 2 h / 50 °C 10: 99 percent / dimethylaminopyridine (DMAP), pyridine / 0.5 h / 25 °C View Scheme

1: LiAlH4 / diethyl ether / 0.33 h / 0 °C 2: ZnBr2, Me3SiBr / CH2Cl2 / 0.5 h / -10 °C 3: 100 percent / pyridinium p-toluenesulfonate (PPTS) / CH2Cl2 / 2 h / 25 °C 4: 90 percent / dimethylformamide / 3 h / 60 °C 5: 1.) n-BuLi, HMPA / 1.) THF, hexane, -15 deg C, 30 min, 2.) THF, hexane, -10 deg C, 30 min 6: dimethylaminopyridine (DMAP) / tetrahydrofuran / 0.83 h / -10 - 25 °C 7: NaOH / diethyl ether; methanol / 0.42 h / 25 °C 8: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / Heating 9: 92 percent / pyridinium p-toluenesulfonate (PPTS) / methanol / 2 h / 50 °C View Scheme