1: 87 percent / immidazole / dimethylformamide / 16 h / Ambient temperature 2: 85 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -35 - -30 °C 3: 17 g / pyridine / 8 h / 0 °C 4: 74 percent / NaHCO3, NaI / acetone / 40 h / Heating 5: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature 6: 79 percent / Na / tetrahydrofuran; liquid ammonia / 1 h 7: 431 mg / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 8: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 9: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 10: 97 percent / PPTS / CH2Cl2 / Ambient temperature 11: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 12: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 13: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 14: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 15: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 90 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 2: 72 percent / Na, NH3 (liquid) / tetrahydrofuran / 1.5 h / -35 °C View Scheme