1: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min 2: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h View Scheme

1: LiAlH4 / diethyl ether / 1 h 2: Me4N(1+)IO4(1-) / CH2Cl2 3: 1.) Me4N(1+)*IO4(1-), 2.) Imidazole, 3.) Na(Hg), Na3PO4, 4.) MCPBA 4: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h 5: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C 6: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 7: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 8: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

1: aq. CH3COOOH, Na2CO3 / CH2Cl2 / 3 h / 0 °C 2: LiAlH4 / diethyl ether / 1 h 3: Me4N(1+)IO4(1-) / CH2Cl2 4: 1.) Me4N(1+)*IO4(1-), 2.) Imidazole, 3.) Na(Hg), Na3PO4, 4.) MCPBA 5: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h 6: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C 7: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 8: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 9: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

1: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 2: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

1: 4-(N,N-dimethlyamino)pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C 2: acetonitrile / 24 h / 20 °C 3: triethylamine; oxygen / acetonitrile / 48 h / 20 °C View Scheme

1: With sodium t-butanolate in tetrahydrofuran; toluene T=70 - 90°C; P=375.038 Torr; 4.41667 h; Inert atmosphere; 2: With hydrogenchloride in dichloromethane; water Cooling with ice; 3: With sodium carbonate in water Reagent/catalystSolventTimeTemperaturePressureConcentration; Overall yield = 37.2 g;

potassium tert-butylate; 1-n-butyl-3-methylimidazolium tetrafluoroborate in tetrahydrofuran T=20°C; 18 h; Molecular sieve; SolventConcentrationReagent/catalystTemperatureTime;

1: With sodium t-butanolate in toluene T=70 - 90°C; P=225.023 - 300.03 Torr; 4.25 h; Inert atmosphere; 2: With hydrogenchloride in dichloromethane; water Cooling with ice; 3: With sodium carbonate in water TimeConcentration;

1: triethylamine / tetrahydrofuran / 2 h / 0 °C 2: tetrahydrofuran / 3 h / -30 °C View Scheme