1: 1.) LiN(iPr)2, 2.) HMPA / 1.) THF, -70 deg C, 10 min, 2.) THF, a) -70 deg C, 7 h, b) 90 deg C, 16 h 2: aq. H2SO4 3: pyridine 4: LiBr / dimethylsulfoxide / 1.5 h / 70 °C 5: 1.) n-BuLi, 2.) HMPA / 1.) THF, from 5 deg C to 10 deg C, 1 h, 2.) THF, 19 h 6: aq. H2SO4 7: PBr3, pyridine / diethyl ether 8: 1.) EtMgBr, 2.) CuI / 1.) THF, 40 deg C, 30 min, 2.) THF, a) 50 deg C, 3 h, b) RT, overnight 9: H2, quinoline / Pd/BaSO4 / ethyl acetate 10: lithium t-butyl thiolate / dimethylformamide View Scheme

1: 13.9 g / Li / tetrahydrofuran / 1.) -10 deg C to 0 deg C, 2.) 0 deg C, overnight 2: 100 percent / conc. HCl / methanol / 24 h 3: 91 percent / H2, H2SO4 / 10percent Pd/C / ethanol 4: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 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