1: 98 percent / LiAlH4 / diethyl ether / 0.25 h / Heating 2: 85 percent / pyridine / diethyl ether 3: CH2Cl2 / 25 °C 4: 1.) O3, 2.) Et2NH / 1.) CH2Cl2, -78 deg C, 2.) reflux, 3 d 5: 93 percent / formic acid / 0.08 h / Heating View Scheme

1.1: Li / diethyl ether / Heating 1.2: 88 percent / diethyl ether / 2 h / 20 °C 2.1: 92 percent / PCC / CH2Cl2 / 3 h / 20 °C 3.1: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C 4.1: 88 percent / m-CPBA / CH2Cl2 / 1.5 h / 0 °C 5.1: 76 percent / SmI2 / tetrahydrofuran; 1,2-dichloro-ethane / 4 h / 80 - 85 °C 6.1: methanol / 4 h / Heating 7.1: 56 mg / LiAlH4 / tetrahydrofuran / 2 h / Heating 8.1: imidazole; NaH / tetrahydrofuran / 0.67 h / 0 °C 8.2: tetrahydrofuran / 1.5 h / 0 °C 8.3: tetrahydrofuran / 1 h / 0 °C 9.1: 11 mg / azobisisobutyronitrile; n-Bu3SnH / toluene / 4 h / Heating View Scheme

palladium on activated charcoal; hydrogen in ethanol P=2280 - 3040 Torr; 0.75 h;

toluene-4-sulfonic acid; [RhCl(η2:η2-cycloocta-1,5-diene)]2 in dichloromethane T=100°C; P=60004.8 Torr; 20 h;

lithium aluminium tetrahydride in diethyl ether T=20°C; Cooling;

lithium carbonate; lithium bromide in N,N-dimethyl-formamide T=130°C; 7 h;

manganese(IV) oxide in hexane

palladium diacetate in acetonitrile 4 h; Ambient temperature;

N,N,N',N',N'',N''-hexamethylphosphoric triamide; potassium tert-butylate in tetrahydrofuran T=-35°C; 2 h;

1.1: AlCl3 / CH2Cl2 / 0.5 h / 0 °C 1.2: 78 percent / CH2Cl2 / 0.17 h / -60 °C 2.1: 50 percent / p-TsOH / [Rh(cod)Cl]2 / CH2Cl2 / 20 h / 100 °C / 60004.8 Torr View Scheme