1: p-TsOH / methanol / 2 h / Heating 2: 95 percent / H2, quinoline / Lindlar catalyst / pentane / 1 h / -10 °C View Scheme

1: p-TsOH / methanol 2: 86 percent / H2 / P2Ni 3: 70 percent / PCC View Scheme

1: TsOH / methanol; H2O / 20 °C 2: 1.) i-BuMgBr, 2.) Cp2TiCl2, 3.) Py / 1.) Et2O, 0 deg C, 15 min, 2.) 20 deg C, 3 h, 3.) 24 h View Scheme

1: p-TsOH / methanol 2: 86 percent / H2 / P2Ni View Scheme

1: p-TsOH / methanol / 2 h / Heating 2: 90 percent / LiAlH4 / 1,2-dimethoxy-ethane / 48 h / 140 °C 3: 95 percent / pyridine / diethyl ether View Scheme

1: lithium; ethylamine / 1 h / -5 °C 2: p-toluenesulfonic acid / ethanol / 3 h / Heating View Scheme

1: 92 percent / PPTS / ethanol / 70 °C 2: 98 percent / H2, quinoline / 5percent Pd/BaSO4 / methanol 3: 89 percent / PCC / CH2Cl2 / 1.5 h View Scheme

1.1: lithium; ethylamine / 1 h / -5 °C 2.1: p-toluenesulfonic acid / ethanol / 3 h / Heating 3.1: iodine; triphenylphosphine; imidazole / diethyl ether; acetonitrile / 1 h / 0 °C 4.1: n-butyllithium / tetrahydrofuran 4.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C 5.1: lithium; ethylamine / 1 h / -5 °C 6.1: p-toluenesulfonic acid / ethanol / 3 h / Heating 7.1: 93 percent / pyridine / 0.5 h / 20 °C View Scheme

pyridinium p-toluenesulfonate in ethanol T=70°C;

lithium; ethylamine T=-5°C; Birch reduction; 1 h;