1: 83 percent / N,N-diethylaniline / CH2Cl2 / 20 h / Ambient temperature 2: 82 percent / NaBH4 / ethanol / 2 h / Ambient temperature 3: 95 percent / NEt3 / CH2Cl2 / 0.25 h / 0 °C 4: 81 percent / KOtBu / tetrahydrofuran / 0.17 h / 0 °C 5: 86 percent / 10percent aq. HCl / methanol / 0.25 h / Ambient temperature 6: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) RT, 2h 7: 42 percent / 10percent aq. HCl / methanol / 0.67 h / 70 °C 8: 1.) DMSO, oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -20 deg C, 20 min, 2.) -20 deg C, 5 min 9: 63 percent / tetrahydrofuran / 1 h / -78 °C 10: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 11: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 1h, 2.) 60 deg C, 1h 12: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme

1: 1.) 2N LiOH, 2.) Ac2O, pyridine / 1.) THF, MeOH, RT, 3h, 2.) benzene, CH2Cl2, RT, 20h 2: 65 percent / 30percent H2O2 / ethyl acetate / 15 - 20 °C 3: 58 percent / OsO4, N-methylmorpholine N-oxide*H2O / acetone; H2O / Ambient temperature 4: 84 percent / p-TsOH / acetone / Ambient temperature 5: 1.) 2N NaOH / 1.) THF, MeOH, RT, 1h, 2.) ether 6: 83 percent / N,N-diethylaniline / CH2Cl2 / 20 h / Ambient temperature 7: 82 percent / NaBH4 / ethanol / 2 h / Ambient temperature 8: 95 percent / NEt3 / CH2Cl2 / 0.25 h / 0 °C 9: 81 percent / KOtBu / tetrahydrofuran / 0.17 h / 0 °C 10: 86 percent / 10percent aq. HCl / methanol / 0.25 h / Ambient temperature 11: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) RT, 2h 12: 42 percent / 10percent aq. HCl / methanol / 0.67 h / 70 °C 13: 1.) DMSO, oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -20 deg C, 20 min, 2.) -20 deg C, 5 min 14: 63 percent / tetrahydrofuran / 1 h / -78 °C 15: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 16: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 1h, 2.) 60 deg C, 1h 17: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme

1: 82 percent / NaBH4 / ethanol / 2 h / Ambient temperature 2: 95 percent / NEt3 / CH2Cl2 / 0.25 h / 0 °C 3: 81 percent / KOtBu / tetrahydrofuran / 0.17 h / 0 °C 4: 86 percent / 10percent aq. HCl / methanol / 0.25 h / Ambient temperature 5: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) RT, 2h 6: 42 percent / 10percent aq. HCl / methanol / 0.67 h / 70 °C 7: 1.) DMSO, oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -20 deg C, 20 min, 2.) -20 deg C, 5 min 8: 63 percent / tetrahydrofuran / 1 h / -78 °C 9: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 10: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 1h, 2.) 60 deg C, 1h 11: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme

1: 63 percent / tetrahydrofuran / 1 h / -78 °C 2: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 3: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 1h, 2.) 60 deg C, 1h 4: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme

1: 81 percent / KOtBu / tetrahydrofuran / 0.17 h / 0 °C 2: 86 percent / 10percent aq. HCl / methanol / 0.25 h / Ambient temperature 3: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) RT, 2h 4: 42 percent / 10percent aq. HCl / methanol / 0.67 h / 70 °C 5: 1.) DMSO, oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -20 deg C, 20 min, 2.) -20 deg C, 5 min 6: 63 percent / tetrahydrofuran / 1 h / -78 °C 7: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 8: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 1h, 2.) 60 deg C, 1h 9: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme

1: 91 percent / pyridine / 13 h / 0 °C 2: 51 percent / NaN3 / dimethylformamide / 0.42 h / 140 - 145 °C 3: 65 percent / H2 / Pd black / ethanol / 14 h / 760 Torr / Ambient temperature 4: 100 percent / K2CO3 / acetone / 1 h / Ambient temperature 5: 80 percent / conc. HCl / methanol / 14 h / Ambient temperature 6: 1.) DMSO, oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -20 deg C, 2.) -20 deg C 7: 1.) CuI, THF-Me2S / 1.) THF, -78 deg C, 2.) -78 deg C 8: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 9: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 2.) 60 deg C 10: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme

1: 42 percent / 10percent aq. HCl / methanol / 0.67 h / 70 °C 2: 1.) DMSO, oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -20 deg C, 20 min, 2.) -20 deg C, 5 min 3: 63 percent / tetrahydrofuran / 1 h / -78 °C 4: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 5: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 1h, 2.) 60 deg C, 1h 6: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme

1: 81 percent / conc. HCl / methanol / 2 h / 40 °C 2: 1.) 2N LiOH, 2.) Ac2O, pyridine / 1.) THF, MeOH, RT, 3h, 2.) benzene, CH2Cl2, RT, 20h 3: 65 percent / 30percent H2O2 / ethyl acetate / 15 - 20 °C 4: 58 percent / OsO4, N-methylmorpholine N-oxide*H2O / acetone; H2O / Ambient temperature 5: 84 percent / p-TsOH / acetone / Ambient temperature 6: 1.) 2N NaOH / 1.) THF, MeOH, RT, 1h, 2.) ether 7: 83 percent / N,N-diethylaniline / CH2Cl2 / 20 h / Ambient temperature 8: 82 percent / NaBH4 / ethanol / 2 h / Ambient temperature 9: 95 percent / NEt3 / CH2Cl2 / 0.25 h / 0 °C 10: 81 percent / KOtBu / tetrahydrofuran / 0.17 h / 0 °C 11: 86 percent / 10percent aq. HCl / methanol / 0.25 h / Ambient temperature 12: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) RT, 2h 13: 42 percent / 10percent aq. HCl / methanol / 0.67 h / 70 °C 14: 1.) DMSO, oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -20 deg C, 20 min, 2.) -20 deg C, 5 min 15: 63 percent / tetrahydrofuran / 1 h / -78 °C 16: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 17: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 1h, 2.) 60 deg C, 1h 18: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme

1: 51 percent / NaN3 / dimethylformamide / 0.42 h / 140 - 145 °C 2: 65 percent / H2 / Pd black / ethanol / 14 h / 760 Torr / Ambient temperature 3: 100 percent / K2CO3 / acetone / 1 h / Ambient temperature 4: 80 percent / conc. HCl / methanol / 14 h / Ambient temperature 5: 1.) DMSO, oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -20 deg C, 2.) -20 deg C 6: 1.) CuI, THF-Me2S / 1.) THF, -78 deg C, 2.) -78 deg C 7: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 8: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 2.) 60 deg C 9: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme

1: 1.) NaH / 1.) THF, DMF, RT, 1h, 2.) RT, 20h 2: 1.) lithium diisopropylamide / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, -78 deg C, 5 min 3: 81 percent / 30percent H2O2 / ethyl acetate / 0.5 h / 15 - 20 °C 4: 11 percent / OsO4, N-methylmorpholine N-oxide*H2O / acetone; H2O / 14 h / Ambient temperature 5: 90 percent / p-TsOH / acetone / 2 h / Ambient temperature 6: 86 percent / H2 / Pd black / ethanol / 13 h / 760 Torr / Ambient temperature 7: 72 percent / borane-Me2S complex / tetrahydrofuran / 1 h / 70 °C 8: 1.) DMSO, oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -20 deg C, 2.) -20 deg C 9: 1.) CuI, THF-Me2S / 1.) THF, -78 deg C, 2.) -78 deg C 10: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 11: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 2.) 60 deg C 12: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme