1: 23.7 percent / pyridine / Ambient temperature 2: 87 percent / immidazole / dimethylformamide / 16 h / Ambient temperature 3: 85 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -35 - -30 °C 4: 17 g / pyridine / 8 h / 0 °C 5: 74 percent / NaHCO3, NaI / acetone / 40 h / Heating 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: 77 percent / LiAlH4 / tetrahydrofuran / 4 h / Ambient temperature 2: 23.7 percent / pyridine / Ambient temperature 3: 87 percent / immidazole / dimethylformamide / 16 h / Ambient temperature 4: 85 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -35 - -30 °C 5: 17 g / pyridine / 8 h / 0 °C 6: 74 percent / NaHCO3, NaI / acetone / 40 h / Heating 7: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature 8: 79 percent / Na / tetrahydrofuran; liquid ammonia / 1 h 9: 431 mg / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 10: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 11: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 12: 97 percent / PPTS / CH2Cl2 / Ambient temperature 13: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 14: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 15: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 16: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 17: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 17 g / pyridine / 8 h / 0 °C 2: 74 percent / NaHCO3, NaI / acetone / 40 h / Heating 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: 96 percent / NaH / dimethylformamide / Ambient temperature 2: 1.43 g / pyridinum bromide perbromide / CHCl3 / 0.67 h / 0 °C 3: 81 percent / NaNH2, Fe(NO3)3 / tetrahydrofuran / 0.5 h 4: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature 5: 79 percent / Na / tetrahydrofuran; liquid ammonia / 1 h 6: 431 mg / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 7: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 8: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 9: 97 percent / PPTS / CH2Cl2 / Ambient temperature 10: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 11: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 12: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 13: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 14: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 83 percent / pyridine / 8 h / 0 °C 3: 1.15 mg / LiAlH4 / diethyl ether / 60 h / 0 °C 4: 96 percent / NaH / dimethylformamide / Ambient temperature 5: 1.43 g / pyridinum bromide perbromide / CHCl3 / 0.67 h / 0 °C 6: 81 percent / NaNH2, Fe(NO3)3 / tetrahydrofuran / 0.5 h 7: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature 8: 79 percent / Na / tetrahydrofuran; liquid ammonia / 1 h 9: 431 mg / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 10: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 11: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 12: 97 percent / PPTS / CH2Cl2 / Ambient temperature 13: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 14: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 15: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 16: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 17: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 1.15 mg / LiAlH4 / diethyl ether / 60 h / 0 °C 2: 96 percent / NaH / dimethylformamide / Ambient temperature 3: 1.43 g / pyridinum bromide perbromide / CHCl3 / 0.67 h / 0 °C 4: 81 percent / NaNH2, Fe(NO3)3 / tetrahydrofuran / 0.5 h 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

2: 89 percent / PPTS / CH2Cl2 / 18 h / Ambient temperature 3: diisobutylalane / toluene; hexane / 0.08 h / -75 °C 4: 52 percent / 1,2-dimethoxy-ethane / 0.08 h / -10 °C 5: 98 percent / i-Pr2NEt / CH2Cl2 / Ambient temperature 6: 94 percent / 75percent AcOH / 0.5 h / 35 °C 7: 83 percent / pyridine / 8 h / 0 °C 9: 1.15 mg / LiAlH4 / diethyl ether / 60 h / 0 °C 10: 96 percent / NaH / dimethylformamide / Ambient temperature 11: 1.43 g / pyridinum bromide perbromide / CHCl3 / 0.67 h / 0 °C 12: 81 percent / NaNH2, Fe(NO3)3 / tetrahydrofuran / 0.5 h 13: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature 14: 79 percent / Na / tetrahydrofuran; liquid ammonia / 1 h 15: 431 mg / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 16: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 17: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 18: 97 percent / PPTS / CH2Cl2 / Ambient temperature 19: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 20: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 21: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 22: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 23: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 74 percent / NaHCO3, NaI / acetone / 40 h / Heating 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: 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: 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