2: 75 percent / H2 / Pd/BaSO4 / hexane / 7 h / 21 °C View Scheme

1: 1.) EtMgBr; 2.) CuCl / 1.) THF, 1 h, reflux; 2.) THF, reflux, 4 h 2: 68 percent / H2 / 10percent Pd-C, quinoline / benzene / Ambient temperature 3: 98 percent / d-camphorsulfonic acid, Et3N / methanol / Ambient temperature 4: 94 percent / pyridine, dimethylaminopyridine / 0 degC then 1 h, room temperature 5: 78 percent / NaI, Na2S2O3 / acetone / Ambient temperature 6: acetonitrile / 11 h, room temperature then 36 h, 40 degC 7: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1.5 h then room temperature, 2 h 8: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature View Scheme

1: potassium carbonate; copper(l) iodide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 2: phosphorus tribromide; pyridine / diethyl ether / 16 h / 0 - 20 °C View Scheme