hydrogen Multistep reaction;

sodium iodide in acetone

1: 2.) H2 2: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 3: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 4: p-TsOH / ethanol / 3 h / Heating 5: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 6: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 7: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme