platinum(IV) oxide; hydrogen in methanol; ethyl acetate T=20°C; 8 h;

Pd/C; hydrogen; ethyl acetate in ethanol T=20°C;

triethylsilane; trifluoroacetic acid in dichloromethane T=0°C; 0.25 h; Inert atmosphere;

1: CSA / CH2Cl2 / 15 °C 2: 70 percent / InCl3 / CH2Cl2 / 22 h / 0 °C 3: 70 percent / Bu3SnH; 1,1'-azobis(cyclohexane carbonitrile) / benzene / 16 h / Heating 4: H2 / Pd/C / methanol; ethyl acetate / 3 h / 20 °C View Scheme

1: 70 percent / InCl3 / CH2Cl2 / 22 h / 0 °C 2: 70 percent / Bu3SnH; 1,1'-azobis(cyclohexane carbonitrile) / benzene / 16 h / Heating 3: H2 / Pd/C / methanol; ethyl acetate / 3 h / 20 °C View Scheme

hydrogenchloride; hydrogen; palladium on activated charcoal in ethanol; water; ethyl acetate 10 h;

hydrogenchloride; water in methanol T=20°C; 12 h; Inert atmosphere;

water; sodium hydroxide in methanol; water T=20°C; 4 h;

1: 98 percent / Bu3SnH; 1,1'-azobis(cyclohexane carbonitrile) / benzene / 16 h / Heating 2: 71 percent / H2 / Pd/C / methanol / 7 h / 20 °C View Scheme

1.1: 73 percent / (S)-BINOL; Ti(OiPr)4; 4 Angstroem MS / CH2Cl2 / 70 h / -20 °C 2.1: 87 percent / imidazole / CH2Cl2 / 4 h / 0 °C 3.1: 85 percent / Mg / methanol / 3 h / 20 °C 4.1: 73 percent / K2CO3 / acetone / 4 h / Heating 5.1: O3 / CH2Cl2 / 1 h / -78 °C 5.2: TPP / CH2Cl2 6.1: CH2Cl2 / 2 h / 20 °C 7.1: 81 percent / Mg / 3 h / 20 °C 8.1: 76 percent / LAH / tetrahydrofuran / 3 h / 0 - 20 °C 9.1: 80 percent / IBX / dimethylsulfoxide / 4 h / 20 °C 10.1: 81 percent / Ba(OH)2*8H2O / tetrahydrofuran; H2O / 5 h / 20 °C 11.1: 80 percent / HF*Py / tetrahydrofuran / 4 h / Heating 12.1: 70 percent / H2; HCl / Pd/C / ethanol; ethyl acetate; H2O / 10 h View Scheme