1: 1.43 g / pyridinum bromide perbromide / CHCl3 / 0.67 h / 0 °C 2: 81 percent / NaNH2, Fe(NO3)3 / tetrahydrofuran / 0.5 h 3: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature 4: 79 percent / Na / tetrahydrofuran; liquid ammonia / 1 h 5: 431 mg / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 6: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 7: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 8: 97 percent / PPTS / CH2Cl2 / Ambient temperature 9: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 10: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 11: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 12: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 13: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

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

1: 81 percent / NaNH2, Fe(NO3)3 / tetrahydrofuran / 0.5 h 2: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature 3: 79 percent / Na / tetrahydrofuran; liquid ammonia / 1 h 4: 431 mg / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 5: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 6: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 7: 97 percent / PPTS / CH2Cl2 / Ambient temperature 8: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 9: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 10: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 11: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 12: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 2: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 3: 97 percent / PPTS / CH2Cl2 / Ambient temperature 4: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 5: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 6: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 7: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 8: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

2: 1.15 mg / LiAlH4 / diethyl ether / 60 h / 0 °C 3: 96 percent / NaH / dimethylformamide / Ambient temperature 4: 1.43 g / pyridinum bromide perbromide / CHCl3 / 0.67 h / 0 °C 5: 81 percent / NaNH2, Fe(NO3)3 / tetrahydrofuran / 0.5 h 6: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature 7: 79 percent / Na / tetrahydrofuran; liquid ammonia / 1 h 8: 431 mg / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 9: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 10: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 11: 97 percent / PPTS / CH2Cl2 / Ambient temperature 12: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 13: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 14: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 15: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 16: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 2: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 2: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 3: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

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

1: 97 percent / PPTS / CH2Cl2 / Ambient temperature 2: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 3: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 4: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 5: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 6: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 2: 97 percent / PPTS / CH2Cl2 / Ambient temperature 3: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 4: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 5: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 6: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 7: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme