1: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature 2: 79 percent / Na / tetrahydrofuran; liquid ammonia / 1 h 3: 431 mg / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 4: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 5: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 6: 97 percent / PPTS / CH2Cl2 / Ambient temperature 7: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 8: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 9: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 10: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 11: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 1.) 1.66M BuLi / 1.) hexane, HMPA, THF, 0 deg C - 5 deg C, 40 min, 2.) hexane, HMPA, THF, r.t., 1 h 2: H2, quinoline / 5percent Pd/BaSO4 / methanol / 760 Torr 3: pyridine / CH2Cl2 / 14 h / 4 °C 4: LiBr, NaHCO3 / acetone / 24 h / Ambient temperature 5: 67 percent / KOH / methanol; aq. ethanol / 3 h / 65 °C 6: 91 percent / 1.0M tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 7: 97 percent / H2 / platinum oxide / hexane; diethyl ether; acetic acid / 96 h / 760 Torr View Scheme