nickel in ethanol Ambient temperature;

1: 100 percent / H2 / Pd/C / methanol / 8 h / 20 °C 2: 1.) sec-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, 0 deg C, 1 h 3: 96 percent / p-TsOH*H2O / benzene / 5 h / 25 °C 4: 95 percent / LDA / tetrahydrofuran / -78 - 20 °C 5: 1.) DMAP, Et3N / 1.) CH2Cl2, 0 deg C, 10 min, 2.) CH2Cl2, 0 deg C, 5 h 6: 1.) O3, 2.) dimethyl sulfide / 1.) MeOH, -78 deg C, 2.) MeOH, 25 deg C, 1 h 7: NaClO2, NaH2PO4 / dimethylsulfoxide; H2O / 25 h / 25 °C 8: 15.6 mg / Raney Ni / ethanol / 0.08 h / 25 °C View Scheme

18-crown-6 ether in acetonitrile T=40°C; 22 h;

1: 90 percent / diisopropylethylamine / CH2Cl2 / 18 h / Heating 2: 61 percent / NaBH4, semicorrin, CoCl2*6H2O / dimethylformamide; ethanol / 4 h / 20 °C 3: triphenylphosphine dibromide / CH2Cl2 / 6 h / 20 °C 4: 18-crown-6 / acetonitrile / 22 h / 40 °C View Scheme

1: 61 percent / NaBH4, semicorrin, CoCl2*6H2O / dimethylformamide; ethanol / 4 h / 20 °C 2: triphenylphosphine dibromide / CH2Cl2 / 6 h / 20 °C 3: 18-crown-6 / acetonitrile / 22 h / 40 °C View Scheme

1: 98 percent / p-toluenesulfonic acid / ethanol; H2O / 18 h / 20 °C 2: 61 percent / NaBH4, semicorrin, CoCl2*6H2O / dimethylformamide; ethanol / 4 h / 20 °C 3: triphenylphosphine dibromide / CH2Cl2 / 6 h / 20 °C 4: 18-crown-6 / acetonitrile / 22 h / 40 °C View Scheme

1: 1.) NaH / 1.) THF, hexane, from -30 deg C to 0 deg C, 1 h, 2.) THF, 0 deg C, 2 h 2: 92 percent / H2, (PPh3)3RhCl / ethanol; benzene / 48 h / 3800 Torr / Ambient temperature 3: 69.5 percent / H2O, phosphate buffer pH=7, pig panereatic lipase, aq. NaOH / diisopropyl ether / 4.33 h / 20 °C 4: CF3COOH / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) RT, 2 h View Scheme

1: 92 percent / H2, (PPh3)3RhCl / ethanol; benzene / 48 h / 3800 Torr / Ambient temperature 2: 69.5 percent / H2O, phosphate buffer pH=7, pig panereatic lipase, aq. NaOH / diisopropyl ether / 4.33 h / 20 °C 3: CF3COOH / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) RT, 2 h View Scheme

1: 69.5 percent / H2O, phosphate buffer pH=7, pig panereatic lipase, aq. NaOH / diisopropyl ether / 4.33 h / 20 °C 2: CF3COOH / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) RT, 2 h View Scheme

1: triphenylphosphine dibromide / CH2Cl2 / 6 h / 20 °C 2: 18-crown-6 / acetonitrile / 22 h / 40 °C View Scheme