1: 96 percent / HCl / 5 h / Heating 2: 96 percent / aq. ammonia / methanol / 48 h / Ambient temperature 3: 40 percent / iodine / diethyl ether / Ambient temperature; Irradiation 4: LAH / tetrahydrofuran / 1.) reflux, 5 h, 2.) r.t. 5: CH2Cl2 / 0.5 h / Ambient temperature 6: 1.) NaH / 1.) THF, r.t., 30 min, 2.) r.t., 2 h 7: 70 percent / LAH, AlCl3 / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 96 percent / aq. ammonia / methanol / 48 h / Ambient temperature 2: 40 percent / iodine / diethyl ether / Ambient temperature; Irradiation 3: LAH / tetrahydrofuran / 1.) reflux, 5 h, 2.) r.t. 4: CH2Cl2 / 0.5 h / Ambient temperature 5: 1.) NaH / 1.) THF, r.t., 30 min, 2.) r.t., 2 h 6: 70 percent / LAH, AlCl3 / tetrahydrofuran / 1.5 h / Heating View Scheme

sodium tetrahydroborate in water

1: CH2Cl2 / 0.5 h / Ambient temperature 2: 1.) NaH / 1.) THF, r.t., 30 min, 2.) r.t., 2 h 3: 70 percent / LAH, AlCl3 / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 40 percent / iodine / diethyl ether / Ambient temperature; Irradiation 2: LAH / tetrahydrofuran / 1.) reflux, 5 h, 2.) r.t. 3: CH2Cl2 / 0.5 h / Ambient temperature 4: 1.) NaH / 1.) THF, r.t., 30 min, 2.) r.t., 2 h 5: 70 percent / LAH, AlCl3 / tetrahydrofuran / 1.5 h / Heating View Scheme

1: LAH / tetrahydrofuran / 1.) reflux, 5 h, 2.) r.t. 2: CH2Cl2 / 0.5 h / Ambient temperature 3: 1.) NaH / 1.) THF, r.t., 30 min, 2.) r.t., 2 h 4: 70 percent / LAH, AlCl3 / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 1.) NaH / 1.) THF, r.t., 30 min, 2.) r.t., 2 h 2: 70 percent / LAH, AlCl3 / tetrahydrofuran / 1.5 h / Heating View Scheme

1.1: sulfuric acid / 0.5 h / |Reflux 2.1: sodium tetrahydroborate; calcium chloride / ethanol / 16 h / 0 - 20 °C 3.1: toluene-4-sulfonic acid / toluene / 18 h / |Dean-Stark; |Reflux 4.1: palladium diacetate; PCy3∙HBF4; potassium carbonate / dimethyl sulfoxide / 0.17 h / 140 °C / 10343.2 Torr / |Microwave irradiation 5.1: hydrogen bromide / 0.5 h / 10 °C 5.2: 2 h / 20 °C 6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 7.1: sodium tris(acetoxy)borohydride / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C View Scheme

1.1: sodium tetrahydroborate; calcium chloride / ethanol / 16 h / 0 - 20 °C 2.1: toluene-4-sulfonic acid / toluene / 18 h / |Dean-Stark; |Reflux 3.1: palladium diacetate; PCy3∙HBF4; potassium carbonate / dimethyl sulfoxide / 0.17 h / 140 °C / 10343.2 Torr / |Microwave irradiation 4.1: hydrogen bromide / 0.5 h / 10 °C 4.2: 2 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 6.1: sodium tris(acetoxy)borohydride / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C View Scheme

1.1: toluene-4-sulfonic acid / toluene / 18 h / |Dean-Stark; |Reflux 2.1: palladium diacetate; PCy3∙HBF4; potassium carbonate / dimethyl sulfoxide / 0.17 h / 140 °C / 10343.2 Torr / |Microwave irradiation 3.1: hydrogen bromide / 0.5 h / 10 °C 3.2: 2 h / 20 °C 4.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 5.1: sodium tris(acetoxy)borohydride / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C View Scheme