1.1: sodium tetrahydroborate / methanol / 0.92 h / -20 - 20 °C / |Inert atmosphere 2.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 12 h / 0 - 40 °C / |Inert atmosphere 3.1: diisobutylaluminium hydride / hexane / 2.17 h / -78 °C / |Inert atmosphere 4.1: manganese(IV) oxide / dichloromethane / 0.5 h / 20 °C / |Inert atmosphere 5.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -30 - -10 °C / |Inert atmosphere 5.2: 1 h / -30 - 20 °C / |Inert atmosphere View Scheme

2: 56 percent / LiI*2H2O, 2,4,6-collidine / 19 h / Heating 3: 1.) O3; 2.) NaBH4 / methanol; 1.) -50 deg C, 0.25 h; 2.) -30 deg C, 1 h 4: pyridine / 18 h / Ambient temperature 5: 81 percent / CrO3 / pyridine; CH2Cl2 / 1.5 h / Ambient temperature 6: 1.) 1.6 M n-BuLi / 1.) Et2O, room temp., 3 h; 2.) THF, reflux, 4 h 7: 71 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h 8: 75 percent / pyridine / 48 h / -20 °C 9: 90 percent / dibenzo-18-crown-6 / acetonitrile / a) room temp., 1 h; b) reflux, 18 h 10: tetrahydrofuran 11: 68 percent / 1 N HCl / Heating View Scheme

1: 100 percent / sodium borohydride / ethanol; H2O / 4 h / Ambient temperature 2: 58 percent / POCl3 / pyridine / 22 h / 95 °C 3: 0.53 g / LiAlH4 / diethyl ether / from -40 to 0 degC over 1 h 4: MnO2 / hexane / 16 h / Ambient temperature View Scheme

dichloro bis(acetonitrile) palladium(II); ytterbium(III) triflate in 1,4-dioxane T=50°C; 5 h;

hydrogenchloride; CuI in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide

dichloro bis(acetonitrile) palladium(II); ytterbium(III) triflate in 1,4-dioxane T=50°C; 24 h;

1.1: NaH / tetrahydrofuran 1.2: 70 percent / n-(C4H9)Li / tetrahydrofuran 2.1: 82 percent / SnCl4 / CH2Cl2 View Scheme

1.1: NaH / tetrahydrofuran 1.2: 70 percent / n-(C4H9)Li / tetrahydrofuran 2.1: 82 percent / SnCl4 / CH2Cl2 View Scheme

1: 65 percent / NaH / diethyl ether / 2 h / Heating 2: 73 percent / SnCl4 / CH2Cl2 / 12 h / Ambient temperature View Scheme

methanol; Lindlar's catalyst Hydrogenation;