1: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 2: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 3: NaOCl / CH2Cl2 / 4 h / Ambient temperature 4: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 5: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 6: 88 percent / tetrahydrofuran / Ambient temperature 8: 1.) CuCN 9: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 10: CrO3, H+ 11: aq. HF / acetonitrile View Scheme

1: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 2: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 3: NaOCl / CH2Cl2 / 4 h / Ambient temperature 4: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 5: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 6: 88 percent / tetrahydrofuran / Ambient temperature View Scheme

1: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 2: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 3: NaOCl / CH2Cl2 / 4 h / Ambient temperature 4: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 5: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 6: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 7: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 8: CrO3, H+ View Scheme

1: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 2: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 3: NaOCl / CH2Cl2 / 4 h / Ambient temperature 4: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 5: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 6: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 7: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 8: CrO3, H+ 10: Bu4NF View Scheme