1: 99 percent / 1N NaOH/MeOH / methanol / 2 h / Heating 2: 29 percent / DDQ / dioxane / 3.5 h / Heating View Scheme

1: 1.) n-BuLi / 1.) hexane, THF, -78 deg C -> 4 deg C; 4 deg C, 2 h, 2.) 4 deg C, 1 h 2: 0.6 g / MeI / acetone; H2O / 24 h / Heating 3: 426 mg / tetrahydrofuran; diethyl ether / 1.) -5-0 deg C -> room temperature, 2.) room temperature, 1 h View Scheme

1: AcNHBr, aq. HBr / H2O; 2-methyl-propan-2-ol 2: Li2CO3 / dimethylformamide 3: (i) NaOEt, DMSO, (ii) NaBH4 View Scheme

1: Li2CO3 / dimethylformamide 2: (i) NaOEt, DMSO, (ii) NaBH4 View Scheme

1.1: 100 percent / diethyl ether; tetrahydrofuran / 0.67 h / 20 °C 2.1: 100 percent / conc. hydrochloric acid / 12 h / 20 °C 3.1: 98 percent / lithium aluminum hydride / 1 h / 20 °C 4.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 5.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 5.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 6.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 7.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 8.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 9.1: pyridine / CHCl3 / 3 h / 20 °C 10.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C 11.1: aq. hydrobromic acid / CHCl3; acetic acid / 1.5 h / 20 °C 11.2: 44 percent / tributyltin hydride; α,α'-azobis(isobutyronitrile) / benzene / 1 h / Heating View Scheme

1.1: 100 percent / conc. hydrochloric acid / 12 h / 20 °C 2.1: 98 percent / lithium aluminum hydride / 1 h / 20 °C 3.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 4.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 4.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 5.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 6.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 7.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 8.1: pyridine / CHCl3 / 3 h / 20 °C 9.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C 10.1: aq. hydrobromic acid / CHCl3; acetic acid / 1.5 h / 20 °C 10.2: 44 percent / tributyltin hydride; α,α'-azobis(isobutyronitrile) / benzene / 1 h / Heating View Scheme

1.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 2.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 3.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 4.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 5.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 6.1: pyridine / CHCl3 / 3 h / 20 °C 7.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C 8.1: aq. hydrobromic acid / CHCl3; acetic acid / 1.5 h / 20 °C 8.2: 44 percent / tributyltin hydride; α,α'-azobis(isobutyronitrile) / benzene / 1 h / Heating View Scheme

1.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 1.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 2.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 3.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 4.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 5.1: pyridine / CHCl3 / 3 h / 20 °C 6.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C 7.1: aq. hydrobromic acid / CHCl3; acetic acid / 1.5 h / 20 °C 7.2: 44 percent / tributyltin hydride; α,α'-azobis(isobutyronitrile) / benzene / 1 h / Heating View Scheme

1.1: pyridine / CHCl3 / 3 h / 20 °C 2.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C 3.1: aq. hydrobromic acid / CHCl3; acetic acid / 1.5 h / 20 °C 3.2: 44 percent / tributyltin hydride; α,α'-azobis(isobutyronitrile) / benzene / 1 h / Heating View Scheme

1.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 2.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 3.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 4.1: pyridine / CHCl3 / 3 h / 20 °C 5.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C 6.1: aq. hydrobromic acid / CHCl3; acetic acid / 1.5 h / 20 °C 6.2: 44 percent / tributyltin hydride; α,α'-azobis(isobutyronitrile) / benzene / 1 h / Heating View Scheme