1: diethyl ether / 5 °C 2: 1.) chromyl chloride / 1.) CH2Cl2, t-BuOH, pyridine, CCl4, -78 deg C, 40 min (prep. of reagent), 2.) CH2Cl2, up to RT, then 35 deg C, 2.5 h 3: 46 percent / 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) -78 deg, 20 min, 3.) THF, -78 deg C, 10 min (adding), then same temp, 2 h 4: 91 percent / H2 / 5percent Pd-C / ethanol / 1.6 h / Ambient temperature 5: 1.) potassium t-butoxide / 1.) benzene, 30 deg C (adding), then 70 deg C, 4 h, 2.) HMPA-H2O, 175 deg C, 15 min 6: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 7: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 8: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 9: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 10: diethyl ether 11: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 12: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 13: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 14: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 15: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme

1: 1.) chromyl chloride / 1.) CH2Cl2, t-BuOH, pyridine, CCl4, -78 deg C, 40 min (prep. of reagent), 2.) CH2Cl2, up to RT, then 35 deg C, 2.5 h 2: 46 percent / 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) -78 deg, 20 min, 3.) THF, -78 deg C, 10 min (adding), then same temp, 2 h 3: 91 percent / H2 / 5percent Pd-C / ethanol / 1.6 h / Ambient temperature 4: 1.) potassium t-butoxide / 1.) benzene, 30 deg C (adding), then 70 deg C, 4 h, 2.) HMPA-H2O, 175 deg C, 15 min 5: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 6: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 7: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 8: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 9: diethyl ether 10: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 11: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 12: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 13: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 14: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme

1: 91 percent / H2 / 5percent Pd-C / ethanol / 1.6 h / Ambient temperature 2: 1.) potassium t-butoxide / 1.) benzene, 30 deg C (adding), then 70 deg C, 4 h, 2.) HMPA-H2O, 175 deg C, 15 min 3: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 4: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 5: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 6: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 7: diethyl ether 8: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 9: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 10: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 11: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 12: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme

1: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 2: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 3: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 4: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 5: diethyl ether 6: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 7: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 8: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 9: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 10: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme

1: 77 percent / N-bromosuccinimide / dimethylsulfoxide; H2O / 15 deg C (adding), then RT, 30 min 2: 89 percent / n-Bu3SnH, azobisisobutyronitrile / benzene / 2 h / Ambient temperature; Irradiation 3: 97 percent / p-toluenesulfonic acid monohydrate / CH2Cl2 / 10 deg C (adding), then RT, 30 min 4: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 5: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 6: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 7: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 8: diethyl ether 9: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 10: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 11: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 12: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 13: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme

1: 89 percent / n-Bu3SnH, azobisisobutyronitrile / benzene / 2 h / Ambient temperature; Irradiation 2: 97 percent / p-toluenesulfonic acid monohydrate / CH2Cl2 / 10 deg C (adding), then RT, 30 min 3: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 4: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 5: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 6: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 7: diethyl ether 8: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 9: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 10: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 11: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 12: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme

1: 1.) potassium t-butoxide, 2.) NaCl / 1.) benzene, 50 deg C (adding), then 65 deg C, 1.5 h, 2.) DMSO-H2O, 120 deg C, 1.5 h 2: 77 percent / N-bromosuccinimide / dimethylsulfoxide; H2O / 15 deg C (adding), then RT, 30 min 3: 89 percent / n-Bu3SnH, azobisisobutyronitrile / benzene / 2 h / Ambient temperature; Irradiation 4: 97 percent / p-toluenesulfonic acid monohydrate / CH2Cl2 / 10 deg C (adding), then RT, 30 min 5: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 6: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 7: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 8: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 9: diethyl ether 10: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 11: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 12: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 13: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 14: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme

1: 97 percent / p-toluenesulfonic acid monohydrate / CH2Cl2 / 10 deg C (adding), then RT, 30 min 2: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 3: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 4: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 5: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 6: diethyl ether 7: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 8: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 9: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 10: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 11: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme

1: 57 percent / hydroquinone / 12 h / 140 °C 2: 1.) potassium t-butoxide, 2.) NaCl / 1.) benzene, 50 deg C (adding), then 65 deg C, 1.5 h, 2.) DMSO-H2O, 120 deg C, 1.5 h 3: 77 percent / N-bromosuccinimide / dimethylsulfoxide; H2O / 15 deg C (adding), then RT, 30 min 4: 89 percent / n-Bu3SnH, azobisisobutyronitrile / benzene / 2 h / Ambient temperature; Irradiation 5: 97 percent / p-toluenesulfonic acid monohydrate / CH2Cl2 / 10 deg C (adding), then RT, 30 min 6: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 7: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 8: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 9: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 10: diethyl ether 11: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 12: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 13: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 14: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 15: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme

1: 99 percent / K2CO3 / acetone / 16 h / 35 °C 2: 57 percent / hydroquinone / 12 h / 140 °C 3: 1.) potassium t-butoxide, 2.) NaCl / 1.) benzene, 50 deg C (adding), then 65 deg C, 1.5 h, 2.) DMSO-H2O, 120 deg C, 1.5 h 4: 77 percent / N-bromosuccinimide / dimethylsulfoxide; H2O / 15 deg C (adding), then RT, 30 min 5: 89 percent / n-Bu3SnH, azobisisobutyronitrile / benzene / 2 h / Ambient temperature; Irradiation 6: 97 percent / p-toluenesulfonic acid monohydrate / CH2Cl2 / 10 deg C (adding), then RT, 30 min 7: 72 percent / H2 / 5percent Pd-C / ethyl acetate / 96 h / Ambient temperature 8: p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 0.17 h / 10 °C 9: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 10: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 11: diethyl ether 12: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 13: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 14: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 15: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 16: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme