1: 75 percent / H2, quinoline / Lindlar catalyst / hexane / 1.5 h / 25 °C / 760 Torr 2: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

1: 85 percent / (-)-pinanyl-9 BBN / tetrahydrofuran / 25 °C 2: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 25 °C 3: 90 percent / AgNO3, KCN / aq. ethanol / 25 °C 4: 1.) (n-C4H9)3SnH, 2.) Br2 / 1.) 130 deg C, 2.) CCl4, -20 deg C 5: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 6: pyridinium chlorochromate / CH2Cl2 / 25 °C 7: sodium bis<trimethylsilyl>amide / 1,2-dimethoxy-ethane / 0 - 25 °C 8: 88 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 25 °C 9: 80 percent / p-toluenesulfonic acid / ethanol / 45 °C 10: 75 percent / H2, quinoline / Lindlar catalyst / hexane / 1.5 h / 25 °C / 760 Torr 11: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

1: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 25 °C 2: 90 percent / AgNO3, KCN / aq. ethanol / 25 °C 3: 1.) (n-C4H9)3SnH, 2.) Br2 / 1.) 130 deg C, 2.) CCl4, -20 deg C 4: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 5: pyridinium chlorochromate / CH2Cl2 / 25 °C 6: sodium bis<trimethylsilyl>amide / 1,2-dimethoxy-ethane / 0 - 25 °C 7: 88 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 25 °C 8: 80 percent / p-toluenesulfonic acid / ethanol / 45 °C 9: 75 percent / H2, quinoline / Lindlar catalyst / hexane / 1.5 h / 25 °C / 760 Torr 10: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

1: 80 percent / p-toluenesulfonic acid / ethanol / 45 °C 2: 75 percent / H2, quinoline / Lindlar catalyst / hexane / 1.5 h / 25 °C / 760 Torr 3: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

1: 1.) (n-C4H9)3SnH, 2.) Br2 / 1.) 130 deg C, 2.) CCl4, -20 deg C 2: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 3: pyridinium chlorochromate / CH2Cl2 / 25 °C 4: sodium bis<trimethylsilyl>amide / 1,2-dimethoxy-ethane / 0 - 25 °C 5: 88 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 25 °C 6: 80 percent / p-toluenesulfonic acid / ethanol / 45 °C 7: 75 percent / H2, quinoline / Lindlar catalyst / hexane / 1.5 h / 25 °C / 760 Torr 8: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

1: 90 percent / AgNO3, KCN / aq. ethanol / 25 °C 2: 1.) (n-C4H9)3SnH, 2.) Br2 / 1.) 130 deg C, 2.) CCl4, -20 deg C 3: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 4: pyridinium chlorochromate / CH2Cl2 / 25 °C 5: sodium bis<trimethylsilyl>amide / 1,2-dimethoxy-ethane / 0 - 25 °C 6: 88 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 25 °C 7: 80 percent / p-toluenesulfonic acid / ethanol / 45 °C 8: 75 percent / H2, quinoline / Lindlar catalyst / hexane / 1.5 h / 25 °C / 760 Torr 9: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

1.1: 70 percent / aq. KHCO3 / 36 h / 23 °C / 49403.3 Torr 2.1: AD-mix-α; CH3SO2NH2; H2O / 2-methyl-propan-2-ol / 36 h / 0 °C 2.2: H2 / Pd-CaCO3 / tetrahydrofuran / 0.67 h / 23 °C / 760.05 Torr 3.1: Et3N / CH2Cl2 / 1 h / 0 °C 4.1: i-Bu2AlH / toluene / 1 h / -78 °C 5.1: HMPA / tetrahydrofuran / 1 h / -25 °C 6.1: aq. LiOH / tetrahydrofuran View Scheme

1.1: AD-mix-α; CH3SO2NH2; H2O / 2-methyl-propan-2-ol / 36 h / 0 °C 1.2: H2 / Pd-CaCO3 / tetrahydrofuran / 0.67 h / 23 °C / 760.05 Torr 2.1: Et3N / CH2Cl2 / 1 h / 0 °C 3.1: i-Bu2AlH / toluene / 1 h / -78 °C 4.1: HMPA / tetrahydrofuran / 1 h / -25 °C 5.1: aq. LiOH / tetrahydrofuran View Scheme

1: Et3N / CH2Cl2 / 1 h / 0 °C 2: i-Bu2AlH / toluene / 1 h / -78 °C 3: HMPA / tetrahydrofuran / 1 h / -25 °C 4: aq. LiOH / tetrahydrofuran View Scheme

1: HMPA / tetrahydrofuran / 1 h / -25 °C 2: aq. LiOH / tetrahydrofuran View Scheme