1: Me4N(1+)IO4(1-) / CH2Cl2 2: 1.) Me4N(1+)*IO4(1-), 2.) Imidazole, 3.) Na(Hg), Na3PO4, 4.) MCPBA 3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h 4: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C 5: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 6: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 7: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

4-(N,N-dimethlyamino)pyridine; triethylamine 3.5 h; Ambient temperature;

sodium tetrahydroborate in methanol; water T=20°C;

1: KOtBu / petroleum ether 2: quinoline 3: aq. HCl / methanol 4: NaBH4 / methanol View Scheme

1: Na2CO3 / acetonitrile / 3 h / 50 °C 2: NaBH4 / methanol View Scheme

1: 94 percent / diisobutylaluminum hydride / diethyl ether / 1) -78 deg C, 1 h; 2) room temperature, 1 h 2: potassium hydride / tetrahydrofuran / 0 °C / Eact.; ΔH8excit.); ΔG(excit.); ΔS(excit.); further temperatures; kanionic/kthermal (25 deg C) View Scheme

1: aq. HCl / methanol 2: NaBH4 / methanol View Scheme

1: quinoline 2: aq. HCl / methanol 3: NaBH4 / methanol View Scheme

potassium hydride in tetrahydrofuran T=-4.5°C; 14 h; Yield given. Yields of byproduct given;

1: NaHCO3; water 2: sodium borate; methanol View Scheme