1: 85 percent / Na2HPO4, 5percent sodium amalgam / ethanol / 1 h 2: 90 percent / imidazole / dimethylformamide / 1 h / Ambient temperature 3: 76 percent / N-methylmorpholine N-oxide monohydrate, 4percent aq. OsO4 / acetonitrile; H2O / 14 h / Ambient temperature 4: 99 percent / pyridinium p-toluenesulfonate / benzene / 13 h / 55 °C 5: 71 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 6: CBr4, PPh3 / CH2Cl2 / 0.33 h / 0 °C 7: Et3N / CH2Cl2 / 0.5 h / 0 °C 8: 86 percent / H2 / PdCl2 / methanol / 0.5 h 9: 66 percent / 2 N aq. HCl / tetrahydrofuran / 14 h / Ambient temperature View Scheme