1.1: Mg / tetrahydrofuran 1.2: 81 percent / tetrahydrofuran / 1 h / 0 - 5 °C 2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 77 percent / tetrahydrofuran; hexane / -60 - 20 °C 3.1: SnCl4 / 1,2-dichloro-ethane / 2 h / 0 - 5 °C 4.1: 77 percent / N-bromosuccinimide; AIBN / benzene / 1 h / Heating 5.1: AcOH; K2CO3 / dimethylformamide / 2 h / 20 °C 5.2: 94 percent / KOH / dimethylformamide; methanol; H2O / 2 h / 20 °C 6.1: 86 percent / SmI2; HMPA / tetrahydrofuran / 2 h / 20 °C 7.1: 79 percent / Ag2CO3-Celite / benzene / 1.5 h / Heating View Scheme

1.1: NaH / tetrahydrofuran; various solvent(s) / 0.33 h / 0 - 20 °C 1.2: n-BuLi / tetrahydrofuran; hexane; various solvent(s) / 0.5 h / -78 °C 1.3: 78 percent / tetrahydrofuran; hexane; various solvent(s) / 0.67 h / -78 °C 2.1: 75 percent / pyridinium chlorochromate; Al2O3 / CH2Cl2 / 0.5 h / 20 °C 3.1: 5 percent / NaOEt / ethanol; tetrahydrofuran / 5 h / 0 °C 4.1: 67 percent / NaH; LiBH4 / dioxane; tetrahydrofuran; various solvent(s) / 28 h / Heating View Scheme

1: 93 percent / potassium trimethylsilanolate / tetrahydrofuran / 5 h / 20 °C 2: 67 percent / NaH; LiBH4 / dioxane; tetrahydrofuran; various solvent(s) / 28 h / Heating View Scheme

1: 100 percent / pTsOH*5H2O / benzene / 3 h / Heating 2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) -78 deg C, 30 min, rt, 2.5 h 3: 0.35 g / acetic anhydride; CH2Cl2; acetic acid / 20 h / 140 °C 4: 51 percent / NaBH4 / tetrahydrofuran / 0.67 h / Ambient temperature View Scheme

1: 0.35 g / acetic anhydride; CH2Cl2; acetic acid / 20 h / 140 °C 2: 51 percent / NaBH4 / tetrahydrofuran / 0.67 h / Ambient temperature View Scheme

1: 75 percent / LiAlH4 / tetrahydrofuran / 1 h / -78 - 0 °C 2: 86 percent / BaMnO4 / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: 60 percent / Br2 / acetic acid / 20 °C 2.1: 87 percent / NaBH4 / tetrahydrofuran / 20 °C 3.1: 78 percent / NaH; BuLi / tetrahydrofuran / -78 °C 4.1: 75 percent / PCC/Al2O3 / CH2Cl2 / 20 °C 5.1: NaOEt / tetrahydrofuran; ethanol / 0 °C 6.1: NaH; LiBH4 / dioxane / 28 h / Heating 6.2: 67 percent / aq. HCl View Scheme

oxygen; mercury(II) trifluoroacetate

mercury(II) trifluoroacetate in tetrahydrofuran 2 h; Ambient temperature;

1: 1.) DDQ, HCl gas, 2.) LiAlH4 / 1.) benzene, reflux, 8 h, 2.) THF, reflux, 6h 2: 30 mg / silica gel - silver carbonate / benzene / 3 h / Heating View Scheme