1: 1.) n-BuLi / 1.) Et2O, 0 deg, 30 min 2: (COCl)2 / 0 - 20 °C 3: pyridine 4: BBr3 / CH2Cl2 / 0.5 h / 0 °C 5: NaH / dimethylformamide 6: 1.) LDA / 1.) THF, -78 deg, 10 min 7: DDQ / dioxane / 0.17 h / 60 °C 8: K2CO3 / dimethylsulfoxide / 16 h / 20 °C 9: LAH / tetrahydrofuran / 1 h / 0 °C 10: pyridine / 24 h 11: imidazole / dimethylformamide / 16 h / 0 - 20 °C 12: TsOH / CH2Cl2; methanol / 0.08 h 13: 62 percent / PCC / CH2Cl2 / 20 °C 14: 91 percent / NBS / CH2Cl2 / 0.5 h / 20 °C 15: MCPBA, Na2SO4, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C 16: aq. NaOH / methanol; tetrahydrofuran / 20 °C 17: K2CO3 / dimethylsulfoxide / 16 h / 20 °C 18: TBAF 19: DEAD, PPh3 20: NaOH 22: 1.) t-BuLi, 2.) FeCl3 / 1.) THF, -78 deg, 2.) -78 deg to 20 deg 23: 1.) TBAF, 2.) H2 / 2.) Pd/C / 1.) THF, 2.) THF, MeOH 24: 65 percent / K3Fe(CN)6, NaOH / H2O; ethanol; tetrahydrofuran / 20 °C 25: 54 percent / DMAP, pyridine 26: aq. HCl View Scheme

1: (COCl)2 / 0 - 20 °C 2: pyridine 3: BBr3 / CH2Cl2 / 0.5 h / 0 °C 4: NaH / dimethylformamide 5: 1.) LDA / 1.) THF, -78 deg, 10 min 6: DDQ / dioxane / 0.17 h / 60 °C 7: K2CO3 / dimethylsulfoxide / 16 h / 20 °C 8: LAH / tetrahydrofuran / 1 h / 0 °C 9: pyridine / 24 h 10: imidazole / dimethylformamide / 16 h / 0 - 20 °C 11: TsOH / CH2Cl2; methanol / 0.08 h 12: 62 percent / PCC / CH2Cl2 / 20 °C 13: 91 percent / NBS / CH2Cl2 / 0.5 h / 20 °C 14: MCPBA, Na2SO4, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C 15: aq. NaOH / methanol; tetrahydrofuran / 20 °C 16: K2CO3 / dimethylsulfoxide / 16 h / 20 °C 17: TBAF 18: DEAD, PPh3 19: NaOH 21: 1.) t-BuLi, 2.) FeCl3 / 1.) THF, -78 deg, 2.) -78 deg to 20 deg 22: 1.) TBAF, 2.) H2 / 2.) Pd/C / 1.) THF, 2.) THF, MeOH 23: 65 percent / K3Fe(CN)6, NaOH / H2O; ethanol; tetrahydrofuran / 20 °C 24: 54 percent / DMAP, pyridine 25: aq. HCl View Scheme

1: pyridine 2: BBr3 / CH2Cl2 / 0.5 h / 0 °C 3: NaH / dimethylformamide 4: 1.) LDA / 1.) THF, -78 deg, 10 min 5: DDQ / dioxane / 0.17 h / 60 °C 6: K2CO3 / dimethylsulfoxide / 16 h / 20 °C 7: LAH / tetrahydrofuran / 1 h / 0 °C 8: pyridine / 24 h 9: imidazole / dimethylformamide / 16 h / 0 - 20 °C 10: TsOH / CH2Cl2; methanol / 0.08 h 11: 62 percent / PCC / CH2Cl2 / 20 °C 12: 91 percent / NBS / CH2Cl2 / 0.5 h / 20 °C 13: MCPBA, Na2SO4, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C 14: aq. NaOH / methanol; tetrahydrofuran / 20 °C 15: K2CO3 / dimethylsulfoxide / 16 h / 20 °C 16: TBAF 17: DEAD, PPh3 18: NaOH 20: 1.) t-BuLi, 2.) FeCl3 / 1.) THF, -78 deg, 2.) -78 deg to 20 deg 21: 1.) TBAF, 2.) H2 / 2.) Pd/C / 1.) THF, 2.) THF, MeOH 22: 65 percent / K3Fe(CN)6, NaOH / H2O; ethanol; tetrahydrofuran / 20 °C 23: 54 percent / DMAP, pyridine 24: aq. HCl View Scheme

1: NaH / dimethylformamide 2: 1.) LDA / 1.) THF, -78 deg, 10 min 3: DDQ / dioxane / 0.17 h / 60 °C 4: K2CO3 / dimethylsulfoxide / 16 h / 20 °C 5: LAH / tetrahydrofuran / 1 h / 0 °C 6: pyridine / 24 h 7: imidazole / dimethylformamide / 16 h / 0 - 20 °C 8: TsOH / CH2Cl2; methanol / 0.08 h 9: 62 percent / PCC / CH2Cl2 / 20 °C 10: 91 percent / NBS / CH2Cl2 / 0.5 h / 20 °C 11: MCPBA, Na2SO4, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C 12: aq. NaOH / methanol; tetrahydrofuran / 20 °C 13: K2CO3 / dimethylsulfoxide / 16 h / 20 °C 14: TBAF 15: DEAD, PPh3 16: NaOH 18: 1.) t-BuLi, 2.) FeCl3 / 1.) THF, -78 deg, 2.) -78 deg to 20 deg 19: 1.) TBAF, 2.) H2 / 2.) Pd/C / 1.) THF, 2.) THF, MeOH 20: 65 percent / K3Fe(CN)6, NaOH / H2O; ethanol; tetrahydrofuran / 20 °C 21: 54 percent / DMAP, pyridine 22: aq. HCl View Scheme

1: 91 percent / NBS / CH2Cl2 / 0.5 h / 20 °C 2: MCPBA, Na2SO4, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C 3: aq. NaOH / methanol; tetrahydrofuran / 20 °C 4: K2CO3 / dimethylsulfoxide / 16 h / 20 °C 5: TBAF 6: DEAD, PPh3 7: NaOH 9: 1.) t-BuLi, 2.) FeCl3 / 1.) THF, -78 deg, 2.) -78 deg to 20 deg 10: 1.) TBAF, 2.) H2 / 2.) Pd/C / 1.) THF, 2.) THF, MeOH 11: 65 percent / K3Fe(CN)6, NaOH / H2O; ethanol; tetrahydrofuran / 20 °C 12: 54 percent / DMAP, pyridine 13: aq. HCl View Scheme

1: 1.) t-BuLi, 2.) FeCl3 / 1.) THF, -78 deg, 2.) -78 deg to 20 deg 2: 1.) TBAF, 2.) H2 / 2.) Pd/C / 1.) THF, 2.) THF, MeOH 3: 65 percent / K3Fe(CN)6, NaOH / H2O; ethanol; tetrahydrofuran / 20 °C 4: 54 percent / DMAP, pyridine 5: aq. HCl View Scheme

1: 1.) TBAF, 2.) H2 / 2.) Pd/C / 1.) THF, 2.) THF, MeOH 2: 65 percent / K3Fe(CN)6, NaOH / H2O; ethanol; tetrahydrofuran / 20 °C 3: 54 percent / DMAP, pyridine 4: aq. HCl View Scheme