1.1: 98 percent / dimethylsulfoxide / 3 h / 20 °C 2.1: zirconocene chloride hydride / benzene / 6 h / 20 °C 2.2: 71 percent / I2 / benzene 3.1: Pd(PPh3)4 / benzene / 0.25 h / 20 °C 3.2: 70 percent / benzene / 20 °C View Scheme

1: 1.) Mg / 1.) THF, 2.) THF, 24 h 2: 81 percent / toluene-4-sulphonic acid / ethanol / 24 h / Heating 3: 1.) KOH, 2.) H2, H2SO4 / 2.) 10percent Pd/C / 1.) ethanol, 1 h, reflux, 2.) ethanol, r.t. 4: 4.31 g / PBr3 / CHCl3 / 4 h / 0 °C 5: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 6: p-TsOH / ethanol / 3 h / Heating 7: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 8: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 9: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

dilithium tetrachlorocuprate; magnesium 1.) THF, 2 h, 2.) 0 deg C, 2 h; Yield given. Multistep reaction;