1: 43 percent / BBr3 / CH2Cl2 / 2.5 h / -78 - -10 °C 2: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 3: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating 4: 87 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 5: 77 percent / aq. potassium nitrosodisulfonate, KH2PO4 / acetone / 0.5 h / Ambient temperature View Scheme

1: KH / tetrahydrofuran / 1.) r.t., 0.5 h, 2.) r.t., 1 h 2: 99 percent / p-TsOH*H2O / acetone; H2O / 4 h / Heating 3: 79 percent / NaH, MeOH / 16 h / Heating 4: 18 percent / SnCl4 / CH2Cl2; H2O / 1.) 0 deg C, 1 h, 2.) r.t., 4 h 5: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 6: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 7: 88 percent / DIBAL / toluene / 0.5 h / -78 °C 8: Et3N / CH2Cl2 / 0.5 h / -78 °C 9: LiBr / tetrahydrofuran; CH2Cl2 / 1 h / -20 °C 10: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h 11: 31 percent / SnCl4 / CH2Cl2; H2O / 2 h / 0 °C 12: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 13: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 14: 94 percent / DIBAL / toluene / 1 h / -78 °C 15: 99 percent / pyridine, DMAP / 0.5 h / 0 °C 16: 1.) n-BuLi, Me3SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h 17: 71 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.5 h / -20 °C 18: 43 percent / BBr3 / CH2Cl2 / 2.5 h / -78 - -10 °C 19: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 20: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating 21: 87 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 22: 77 percent / aq. potassium nitrosodisulfonate, KH2PO4 / acetone / 0.5 h / Ambient temperature View Scheme

1: 79 percent / NaH, MeOH / 16 h / Heating 2: 18 percent / SnCl4 / CH2Cl2; H2O / 1.) 0 deg C, 1 h, 2.) r.t., 4 h 3: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 4: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 5: 88 percent / DIBAL / toluene / 0.5 h / -78 °C 6: Et3N / CH2Cl2 / 0.5 h / -78 °C 7: LiBr / tetrahydrofuran; CH2Cl2 / 1 h / -20 °C 8: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h 9: 31 percent / SnCl4 / CH2Cl2; H2O / 2 h / 0 °C 10: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 11: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 12: 94 percent / DIBAL / toluene / 1 h / -78 °C 13: 99 percent / pyridine, DMAP / 0.5 h / 0 °C 14: 1.) n-BuLi, Me3SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h 15: 71 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.5 h / -20 °C 16: 43 percent / BBr3 / CH2Cl2 / 2.5 h / -78 - -10 °C 17: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 18: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating 19: 87 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 20: 77 percent / aq. potassium nitrosodisulfonate, KH2PO4 / acetone / 0.5 h / Ambient temperature View Scheme

1: nBu4NF / tetrahydrofuran / 1.) 40 deg C, 20 h, 2.) r.t., 48 h 2: KH / tetrahydrofuran / 1.) r.t., 0.5 h, 2.) r.t., 1 h 3: 99 percent / p-TsOH*H2O / acetone; H2O / 4 h / Heating 4: 79 percent / NaH, MeOH / 16 h / Heating 5: 18 percent / SnCl4 / CH2Cl2; H2O / 1.) 0 deg C, 1 h, 2.) r.t., 4 h 6: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 7: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 8: 88 percent / DIBAL / toluene / 0.5 h / -78 °C 9: Et3N / CH2Cl2 / 0.5 h / -78 °C 10: LiBr / tetrahydrofuran; CH2Cl2 / 1 h / -20 °C 11: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h 12: 31 percent / SnCl4 / CH2Cl2; H2O / 2 h / 0 °C 13: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 14: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 15: 94 percent / DIBAL / toluene / 1 h / -78 °C 16: 99 percent / pyridine, DMAP / 0.5 h / 0 °C 17: 1.) n-BuLi, Me3SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h 18: 71 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.5 h / -20 °C 19: 43 percent / BBr3 / CH2Cl2 / 2.5 h / -78 - -10 °C 20: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 21: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating 22: 87 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 23: 77 percent / aq. potassium nitrosodisulfonate, KH2PO4 / acetone / 0.5 h / Ambient temperature View Scheme

1: 99 percent / p-TsOH*H2O / acetone; H2O / 4 h / Heating 2: 79 percent / NaH, MeOH / 16 h / Heating 3: 18 percent / SnCl4 / CH2Cl2; H2O / 1.) 0 deg C, 1 h, 2.) r.t., 4 h 4: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 5: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 6: 88 percent / DIBAL / toluene / 0.5 h / -78 °C 7: Et3N / CH2Cl2 / 0.5 h / -78 °C 8: LiBr / tetrahydrofuran; CH2Cl2 / 1 h / -20 °C 9: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h 10: 31 percent / SnCl4 / CH2Cl2; H2O / 2 h / 0 °C 11: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 12: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 13: 94 percent / DIBAL / toluene / 1 h / -78 °C 14: 99 percent / pyridine, DMAP / 0.5 h / 0 °C 15: 1.) n-BuLi, Me3SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h 16: 71 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.5 h / -20 °C 17: 43 percent / BBr3 / CH2Cl2 / 2.5 h / -78 - -10 °C 18: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 19: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating 20: 87 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 21: 77 percent / aq. potassium nitrosodisulfonate, KH2PO4 / acetone / 0.5 h / Ambient temperature View Scheme

1: 18 percent / SnCl4 / CH2Cl2; H2O / 1.) 0 deg C, 1 h, 2.) r.t., 4 h 2: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 3: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 4: 88 percent / DIBAL / toluene / 0.5 h / -78 °C 5: Et3N / CH2Cl2 / 0.5 h / -78 °C 6: LiBr / tetrahydrofuran; CH2Cl2 / 1 h / -20 °C 7: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h 8: 31 percent / SnCl4 / CH2Cl2; H2O / 2 h / 0 °C 9: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 10: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 11: 94 percent / DIBAL / toluene / 1 h / -78 °C 12: 99 percent / pyridine, DMAP / 0.5 h / 0 °C 13: 1.) n-BuLi, Me3SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h 14: 71 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.5 h / -20 °C 15: 43 percent / BBr3 / CH2Cl2 / 2.5 h / -78 - -10 °C 16: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 17: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating 18: 87 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 19: 77 percent / aq. potassium nitrosodisulfonate, KH2PO4 / acetone / 0.5 h / Ambient temperature View Scheme

1: LiBr / tetrahydrofuran; CH2Cl2 / 1 h / -20 °C 2: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h 3: 31 percent / SnCl4 / CH2Cl2; H2O / 2 h / 0 °C 4: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 5: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 6: 94 percent / DIBAL / toluene / 1 h / -78 °C 7: 99 percent / pyridine, DMAP / 0.5 h / 0 °C 8: 1.) n-BuLi, Me3SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h 9: 71 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.5 h / -20 °C 10: 43 percent / BBr3 / CH2Cl2 / 2.5 h / -78 - -10 °C 11: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 12: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating 13: 87 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 14: 77 percent / aq. potassium nitrosodisulfonate, KH2PO4 / acetone / 0.5 h / Ambient temperature View Scheme

1: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 2: 88 percent / DIBAL / toluene / 0.5 h / -78 °C 3: Et3N / CH2Cl2 / 0.5 h / -78 °C 4: LiBr / tetrahydrofuran; CH2Cl2 / 1 h / -20 °C 5: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h 6: 31 percent / SnCl4 / CH2Cl2; H2O / 2 h / 0 °C 7: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 8: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 9: 94 percent / DIBAL / toluene / 1 h / -78 °C 10: 99 percent / pyridine, DMAP / 0.5 h / 0 °C 11: 1.) n-BuLi, Me3SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h 12: 71 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.5 h / -20 °C 13: 43 percent / BBr3 / CH2Cl2 / 2.5 h / -78 - -10 °C 14: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 15: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating 16: 87 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 17: 77 percent / aq. potassium nitrosodisulfonate, KH2PO4 / acetone / 0.5 h / Ambient temperature View Scheme

1: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 2: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 3: 88 percent / DIBAL / toluene / 0.5 h / -78 °C 4: Et3N / CH2Cl2 / 0.5 h / -78 °C 5: LiBr / tetrahydrofuran; CH2Cl2 / 1 h / -20 °C 6: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h 7: 31 percent / SnCl4 / CH2Cl2; H2O / 2 h / 0 °C 8: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h 9: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h 10: 94 percent / DIBAL / toluene / 1 h / -78 °C 11: 99 percent / pyridine, DMAP / 0.5 h / 0 °C 12: 1.) n-BuLi, Me3SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h 13: 71 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.5 h / -20 °C 14: 43 percent / BBr3 / CH2Cl2 / 2.5 h / -78 - -10 °C 15: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 16: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating 17: 87 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 18: 77 percent / aq. potassium nitrosodisulfonate, KH2PO4 / acetone / 0.5 h / Ambient temperature View Scheme

1: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 2: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating 3: 87 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 4: 77 percent / aq. potassium nitrosodisulfonate, KH2PO4 / acetone / 0.5 h / Ambient temperature View Scheme