1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 2: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 3: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 4: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 5: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

N,N,N',N',N'',N''-hexamethylphosphoric triamide in tetrahydrofuran; hexane T=-65°C;

dipyridinium dichromate in dichloromethane 41 h; Ambient temperature;

tetra(n-butyl)ammonium hydrogensulfate; silver carbonate; palladium diacetate in acetonitrile T=70°C; 4 h;

hydrogenchloride in acetone T=60°C; Hydrolysis;

hydrogenchloride in acetone 6 h; Ambient temperature;

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 42 percent / hexamethylphosphoric acid triamide / tetrahydrofuran; hexane / -78 - 20 °C 2.1: 81 percent / H2, quinoline / Pd-CaCO3 / hexane / 1 h 3.1: 44 percent / aq. HCl / acetone / 60 °C View Scheme

1: 81 percent / H2, quinoline / Pd-CaCO3 / hexane / 1 h 2: 44 percent / aq. HCl / acetone / 60 °C View Scheme

1: 1.) Mg, 2.) methyl Grignard reagent / 2.) bis(diphenylphosphino)propanenickel(II) chloride / 1.) Et2O, 2.) C6H6, reflux, overnight 2: 54 percent / PCC / CH2Cl2 / 4 h / 25 °C View Scheme

1: 1.) Mg, 2.) methyl Grignard reagent / 2.) bis(diphenylphosphino)propanenickel(II) chloride / 1.) Et2O, 2.) C6H6, reflux, overnight 2: 54 percent / PCC / CH2Cl2 / 4 h / 25 °C View Scheme