1: 92 percent / p-TsOH / 24 h / Ambient temperature 2: 70 percent / TEA / dimethylformamide / 18 h / Ambient temperature View Scheme

1: 92 percent / p-TsOH / 24 h / Ambient temperature 2: 70 percent / TEA / dimethylformamide / 18 h / Ambient temperature 4: DIBAL-H / toluene / 1 h / -78 °C 5: 80 percent / N-chlorosuccinimide-dimethylsulfide complex / CH2Cl2 / -25 - 0 °C 6: 1.) nBuLi 2.) H2O2 / 1.) a) 0 deg C b) -78 deg C, 30 min 2.) CHCl3 View Scheme

1: 85 percent / conc. sulphuric acid / 1 h / Heating 2: NaBH4 / ethanol / 12 h 3: 82 percent / sodium periodate / ethanol; H2O / 0.25 h 4: 90 percent / pyridine / 1.) cooling with CCl4-solid CO2, 25 min, 2.) room temperature, overnight 5: 26 percent / p-TsOH / benzene / 10 h / Heating View Scheme

1: 100 percent / acetyl chloride / 1 h / Heating 2: 74 percent / NH3 / methanol / 48 h 3: 1.) hydrogen chloride, 2.) lead carbonate, MgSO4 / 1.) 48 h, 2.) 2 h 4: 86 percent / pyridine / 48 h / Ambient temperature 5: 82 percent / AcOH / H2O / 2 h / 60 - 70 °C View Scheme

1: 93 percent / p-toluenesulfonic acid / dimethylformamide; benzene / 25 h / Heating 2: 76 percent / pyridine / 2 h / 20 °C View Scheme

1: 97 percent / p-TsOH / benzene / 19 h / Heating 2: 76 percent / N-bromosuccinimide / CCl4 / 1.3 h 3: 1.) NaBH4, 2.) p-TsOH / 1.) i-PrOH, 2.) acetone, reflux, 2 h 4: 64 percent / PCC / CH2Cl2 / 11 h / Heating 5: 88 percent / dimethylformamide / 15 h / 25 °C 6: 99 percent / diethyl ether; ethyl acetate / 15 h / 0 °C 7: 62 percent / (i-Bu)2AlH / CH2Cl2 / 3 h / 0 °C 8: PCC, NaOAc / CH2Cl2 / 13 h / 25 °C 9: NaN3 / LiCl / dimethylformamide / 15 h / 25 °C 10: 94 percent / diethyl ether / 3 h / 25 °C 11: 2.) NaBH3CN / 1.) Et2O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h 12: NaBH4 / methanol; H2O / 3 h / 0 °C 13: 50percent aq. TFA / 0.33 h / 0 °C View Scheme

1: 2) Dowex 50WX8 (H+) / 1) DMF, benzene, reflux, 3 h, 2) reflux, 24 h 2: 96 percent / methanol / 1 h / 0 °C 3: 1) oxalyl chloride, DMSO, 2) triethylamine / 1) CH2Cl2, 40 min, -60 deg C, 2) 10 min, -60 deg C 4: POCl3, pyridine / Ambient temperature 5: 82 percent / NaBH4 / methanol / 1.5 h / 0 °C 6: 82 percent / OsO4, trimethylamine-N-oxide, pyridine, water / 2-methyl-propan-2-ol / 12 h / Heating 7: 100 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature 8: 86 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 1) -78 deg C, 1 h, 2) to 0 deg C, 12 h 9: 71 percent / triethylamine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 6 h / 0 °C 10: 75 percent / diisobutylaluminium hydride (DIBAL-H) / tetrahydrofuran / 1 h / 0 °C 11: 95 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature 12: 80 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 12 h / Ambient temperature 13: 100 percent / 50percent aq. CF3COOH / 4 h / Ambient temperature View Scheme

hydrogen bromide T=130°C; im geschlossenen Rohr;

T=115 - 120°C; im geschlossenen Rohr;

T=130°C; im Druckrohr;