1: AcOH / methanol / 6 h / 40 °C 2: imidazole / dimethylformamide / 10 h / Ambient temperature 3: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 4: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 5: NaOCl / CH2Cl2 / 4 h / Ambient temperature 6: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 7: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 8: 88 percent / tetrahydrofuran / Ambient temperature 10: 1.) CuCN 11: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 12: CrO3, H+ 13: aq. HF / acetonitrile View Scheme

1: AcOH / methanol / 6 h / 40 °C 2: imidazole / dimethylformamide / 10 h / Ambient temperature 3: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 4: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 5: NaOCl / CH2Cl2 / 4 h / Ambient temperature 6: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 7: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 8: 88 percent / tetrahydrofuran / Ambient temperature View Scheme

1: AcOH / methanol / 6 h / 40 °C 2: imidazole / dimethylformamide / 10 h / Ambient temperature 3: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 4: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 5: NaOCl / CH2Cl2 / 4 h / Ambient temperature 6: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 7: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 8: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 9: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 10: CrO3, H+ View Scheme

1: AcOH / methanol / 6 h / 40 °C 2: imidazole / dimethylformamide / 10 h / Ambient temperature 3: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 4: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 5: NaOCl / CH2Cl2 / 4 h / Ambient temperature 6: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 7: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 8: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 9: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 10: CrO3, H+ 12: Bu4NF View Scheme