1: H2 / Pd 2: DIBAL 3: p-TSA View Scheme

1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: DIBAL 2: p-TSA View Scheme

1.1: magnesium / tetrahydrofuran / 3 h / 55 °C 1.2: dilithium tetrachlorocuprate(II) / tetrahydrofuran / 3 h / 0 °C 2.1: 4.5 g / pyridinium p-toluenesulfonate / methanol / 3 h / Heating View Scheme

1: 1) magnesium, 2) Li2CuCl4 / 1) THF, 2) room temperature, 3 h 2: NaOH / ethanol / 2 h / Heating 3: 2 N HCl / ethanol / 1 h / Heating View Scheme

1: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 2: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 3: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 4: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature View Scheme