1: liquid ammonia 2: potassium iodide; ethanol / Behandeln der Reaktionsloesung mit wss.Kalilauge View Scheme

1: liquid ammonia 2: ethanol / Erhitzen der Reaktionsloesung mit wss.Natronlauge 3: platinum; ethyl acetate / Hydrogenation View Scheme

1: 73 percent / [(CH3)3Si]2NNa; HMPA / tetrahydrofuran / 2.5 h / -78 - 20 °C 2: 87 percent / CF3CO2H / CH2Cl2 / 4 h / 25 °C 3: 45 percent / K2CO3; KI / acetonitrile / 24 h / Heating 4: 96 percent / PdCl2; H2 / tetrahydrofuran; ethanol / 20 h / 2585.74 Torr 5: 60 percent / Et3N / tetrahydrofuran; H2O / 16 h / 20 °C View Scheme

1.1: BuLi / tetrahydrofuran / 0.5 h / 20 °C 1.2: 33 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 20 °C 2.1: 82 percent / NaI / acetone / 48 h / Heating 3.1: 66 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -50 °C 4.1: 84 percent / p-TsOH / methanol / 16 h / 20 °C 5.1: 97 percent / Na(Hg); Na2HPO4 / methanol / 21 h / 20 °C View Scheme

1: tetrahydrofuran; hexamethylphosphoric acid triamide / 0 - 20 °C 2: K2CO3 / methanol / 20 °C 3: NaI / acetone / 48 h / 80 °C View Scheme

1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 30 h / 23 °C 2: NaI / acetone / 65 h / Heating 3: 1.) Mg, 2.) CuI / 1.) THF, reflux, 3 h, 2.) 30 min, ice bath, 3.) 23 deg C, 30 min 4: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 23 °C 5: 68 percent / CrO3, 6 N H2SO4 / acetone / 3.5 h, ice-cold then RT 6: diethyl ether View Scheme

1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 30 h / 23 °C 2: NaI / acetone / 65 h / Heating 3: 1.) Mg, 2.) CuI / 1.) THF, reflux, 3 h, 2.) 30 min, ice bath, 3.) 23 deg C, 30 min 4: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 23 °C 5: 68 percent / CrO3, 6 N H2SO4 / acetone / 3.5 h, ice-cold then RT 6: 1.) sodium borohydride, 2.) 5percent HCl / 1.) ethanol, 5 min, 2.) RT View Scheme

1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 30 h / 23 °C 2: NaI / acetone / 65 h / Heating 3: 1.) Mg, 2.) CuI / 1.) THF, reflux, 3 h, 2.) 30 min, ice bath, 3.) 23 deg C, 30 min 4: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 23 °C 5: 68 percent / CrO3, 6 N H2SO4 / acetone / 3.5 h, ice-cold then RT 6: 1.) sodium borohydride, 2.) 5percent HCl / 1.) ethanol, 5 min, 2.) RT 7: 1.) sodium borohydride, ethylenediamine 2.) 5percent HCl / P-2 nickel / 1.) ethanol, 23 deg C, 1 h View Scheme

1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 30 h / 23 °C 2: NaI / acetone / 65 h / Heating 3: 1.) Mg, 2.) CuI / 1.) THF, reflux, 3 h, 2.) 30 min, ice bath, 3.) 23 deg C, 30 min 4: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 23 °C 5: 68 percent / CrO3, 6 N H2SO4 / acetone / 3.5 h, ice-cold then RT 6: 1.) sodium borohydride, 2.) 5percent HCl / 1.) ethanol, 5 min, 2.) RT 7: 1.) sodium borohydride, ethylenediamine 2.) 5percent HCl / P-2 nickel / 1.) ethanol, 23 deg C, 1 h 8: 30 percent / 2,2'-dipyridyl disulfide, triphenylphosphine, silver perchlorate / 1.) THF, 1.5 h, 23 deg C, 2.) xylene, 10 h, reflux View Scheme

1: DMF 2: acetone; CuI; NaI 3: acetic acid 4: ethanolic KOH View Scheme