1: 77 percent / PBr3, pyridine / diethyl ether / Ambient temperature 2: 60 percent / benzene / 12 h / Heating 3: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 4: 76 percent / LAH, EtOH / diethyl ether 5: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 6: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 7: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 8: 70 percent / LAH, EtOH / diethyl ether View Scheme

1: triethylamine / dichloromethane / 1 h / 0 °C / |Inert atmosphere 2: potassium carbonate; copper(l) iodide; sodium iodide / N,N-dimethyl-formamide / 18 h / 20 °C / |Inert atmosphere 3: KF*2H2O / N,N-dimethyl-formamide / 4 h / 20 °C / |Inert atmosphere View Scheme

2: 1) NaH / 1) allylalcohol, mineral oil, 90 deg C, 3 h; 2) 100 deg C, 3-4 h 3: 85 percent Chromat. / Pd(OAc)2, PPh3 / acetonitrile / 0.5 h / 80 °C / Heating; effect and amount of different catalyst and solvent 4: 95 percent / H2 / Lindlar catalyst / butan-1-ol / 2 h / 760 Torr / Ambient temperature 5: NaOMe / methanol / 10 h / 0 °C View Scheme

1: triphenyl phosphite, I2, imidazol / diethyl ether; acetonitrile / 0.67 h / 25 °C 2: Cu(I) 3: 90 percent / tetrahydrofuran / 12 h / 65 °C 4: 91 percent / LiAlH4 / diethyl ether / 5 h / 25 °C 5: 76 percent / dimethyl(S,S)(-)-tartarate 6: 90 percent / H2 / Lindlar / tetrahydrofuran / 760 Torr 7: 84 percent / O2 / oxidation with Collins reagent 8: 94 percent / tetrahydrofuran / -78 deg C, 10 min,; and then from -78 deg Cto 0 deg C over 1 h. 9: 84 percent / acetic acid; acetonitrile; H2O / 6 h / 25 °C 10: triphenylphosphine, imidazole, I2, diisopropylamine / diethyl ether; acetonitrile / 0.67 h / 25 °C 11: acetonitrile / 16 h / 60 °C 13: 1.) potassium isopropoxide; 2.) base / 1.) 0 deg C, 1 h; 2.) hydrolysis View Scheme

triethylamine in dichloromethane T=-5°C; 0.416667 h;

1.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 5 h / 20 °C / |Inert atmosphere 2.1: dicobalt octacarbonyl / hexane / 1 h / |Inert atmosphere 2.2: 20 °C / 4500.45 Torr / |Inert atmosphere; |Molecular sieve 3.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / |Inert atmosphere 4.2: -78 °C / |Inert atmosphere View Scheme

2: 1) NaH / 1) allylalcohol, mineral oil, 90 deg C, 3 h; 2) 100 deg C, 3-4 h View Scheme

sodium tetrahydroborate; mercury(II) diacetate 1.) THF, 0 deg C, 5 min; 2.) 1:1=THF:H2O, NaOH; Yield given. Multistep reaction;

1: 90 percent / quinoline; H2 / Lindlar's catalyst / hexane 2: 60 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h / 10 °C 3: 80 percent / diethyl ether / 1.) stirring, 2 h, 2.) left overnight, 3.) reflux, 2 h 4: 50 percent / mercuric acetate / 16 h / Heating View Scheme

sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride in dichloromethane 0.333333 h; Ambient temperature;