1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C View Scheme

sodium hydroxide in ammonia T=50°C; 48 h; in a titanium autoclave; Yield given;

1: 86 percent / 1.) hexamethylphosphoric triamide, BuLi / tetrahydrofuran; hexane / -70 - 0 °C 2: 1.) Li in EtNH2; 2.) oxygen / 1.) THF, -70 deg C; 2.) THF, MeOH, H2O, Et2O View Scheme

1: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C, 3 h 2: Li, ethylamine / diethyl ether / 2.5 h / -78 °C View Scheme

1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 3: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 4: 78 percent / dimethylformamide / 24 h / Ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 70 percent / Li, ethylamine / diethyl ether 10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 11: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

1: (i) nBuLi, (ii) /BRN= 2321514/ 2: (i) Li, EtNH2, (ii) aq. FeCl3, AcOH View Scheme

carbon tetrabromide; tetra-(n-butyl)ammonium iodide in tetrahydrofuran T=20°C; 24 h;

1: pyridine / tetrahydrofuran / 4 h / 0 °C 2: Ph3P / tetrakis(triphenylphosphine)palladium / tetrahydrofuran / 26 h / 0 °C View Scheme

triphenylphosphine; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=0°C; 26 h; Yield given. Yields of byproduct given;

1: pyridine / tetrahydrofuran / 4 h / 0 °C 2: Ph3P / tetrakis(triphenylphosphine)palladium / tetrahydrofuran / 26 h / 0 °C View Scheme