piperidine; sulfuric acid 1) pyridine; Yield given. Multistep reaction;

potassium tert-butylate 1.) THF, -20 deg C, 2.) -20 deg C, 1 h; Yield given. Multistep reaction;

1: pyridine; piperidine / 30 h / |Heating 2: sulfuric acid / 4 h / |Cooling with ice; |Reflux View Scheme

sodium hydride 1.) 1,2-dimethoxyethane, 20 deg C, 2.) 1,2-dimethoxyethane, 10 deg C, 4 h, 60 deg C, 1 h; Yield given. Multistep reaction;

1: 93 percent / BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 10 min, 2.) -78 deg C to 20 deg C, 0.5 h 2: 95 percent / H2 / Lindlar catalyst / ethyl acetate / 3 h 3: 65 percent / NaH / 1.) 0.5 h, 2.) DMSO, 0-20 deg C, 0.5 h 4: 77 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C 5: 84 percent / KOH / methanol / 2.5 h / 20 °C 6: 66 percent / Et3N, 2-chloro-1-methylpyridinium iodide / acetonitrile / 4 h / 80 °C 7: 84 percent / LDA, TMSCl / tetrahydrofuran; hexane / 1.) -100 to -30 deg C, 2.) -30 to 20 deg C, 1 h 8: 86 percent / diethyl ether / 1 h / 20 °C 9: 98 percent / CHCl3 / 24 h / 20 °C 10: LiAlH4 / tetrahydrofuran / 0 - 20 °C 11: pyridine / 15 h / 20 °C 12: OsO4, NMMO, H2O / 2-methyl-propan-2-ol; acetone / 16 h / 20 °C 13: 94 percent / NaIO4, Bu4NIO4 / CH2Cl2; H2O / 48 h 14: 58 percent / NaBH4 / methanol / 1 h / 0 °C 15: 83 percent / (i-Pr)2NEt / tetrahydrofuran / 72 h / 20 °C 16: 83 percent / KOH / methanol / 2 h / 0 - 20 °C 17: 81 percent / TPAP, NMMO, molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 24 h / 20 °C 18: 73 percent / HCl, H2O / tetrahydrofuran / 48 h / 20 °C View Scheme

1: 82 percent / KOH / ethanol / 12 h / Ambient temperature 2: 75 percent / glacial acetic acid, H3PO4 / 0.33 h / 100 °C View Scheme

1: 51 percent / n-BuLi, N,N,N'-trimethylethylenediamine / tetrahydrofuran; hexane / 1.) -20 deg C, 15 min; -20 deg C, 3 h, 2.) r.t., overnight 2: aq. NaClO2, NaH2PO4*H2O, 2-methyl-2-butene / 2-methyl-propan-2-ol / 16 h / Ambient temperature 3: (COCl)2 / CH2Cl2 / 3 h / Ambient temperature 4: aq. NaN3 / benzene / 1.) 0 deg C, 15 min, 2.) r.t., 1 h 5: toluene / 1 h / Heating 6: 68 percent / Et3N, Cl3SiH / CH2Cl2 / 1.) 0 deg C, 1.5 h, 2.) r.t., 30 min 7: 53 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation 8: 76 percent / TFA / 10 h / Heating View Scheme

sodium hydroxide; acetaldehyde

barium dihydroxide in tetrahydrofuran Condensation; Cross aldol condensation; 10 h; Heating;

in toluene T=95°C; Wittig olefination; Inert atmosphere;