hydrogen; Lindlar's catalyst T=21°C; 15 h;

1: H2 / Lindlar's catalyst / ethyl acetate 2: camphorsulfonic acid / methanol 3: CBr4, triphenylphosphine / acetonitrile 4: NaI / acetone View Scheme

1: NaH / tetrahydrofuran / 2 h / 0 °C 2: AcOH / methanol / 6 h / 40 °C 3: imidazole / dimethylformamide / 10 h / Ambient temperature 4: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 5: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 6: NaOCl / CH2Cl2 / 4 h / Ambient temperature 7: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 8: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 9: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 10: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 11: 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+ 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: NaOCl / CH2Cl2 / 4 h / Ambient temperature 2: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 3: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 4: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 5: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 6: CrO3, H+ View Scheme

1: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 2: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 3: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 4: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 5: CrO3, H+ View Scheme

2: pyridine / 0 - 5 °C 3: pyridine / 0 - 5 °C 4: 42 percent / m-chloroperbenzoic acid / -78 - 20 °C 5: 89 percent / hydrogen / Lindlar catalyst / 15 h / 21 °C View Scheme

2: pyridine / 0 - 5 °C 3: pyridine / 0 - 5 °C 4: 42 percent / m-chloroperbenzoic acid / -78 - 20 °C 5: 89 percent / hydrogen / Lindlar catalyst / 15 h / 21 °C View Scheme

1: pyridine / 0 - 5 °C 2: pyridine / 0 - 5 °C 3: 42 percent / m-chloroperbenzoic acid / -78 - 20 °C 4: 89 percent / hydrogen / Lindlar catalyst / 15 h / 21 °C View Scheme