1: With diisobutylaluminium hydride in hexane; Petroleum ether T=-60 - 20°C; 0.5 h; 2: With silica gel in water; toluene T=-20 - 0°C; 1 h;

1: 25 percent / NaOAc / acetic acid / 0.25 h / Ambient temperature 2: 65 percent / trifluoroacetic acid / CH2Cl2 / 0.25 h / 0 °C 3: 46.2 percent / 30percent H2O2 / methanol / 0.17 h / 0 °C 4: 93 percent / CCl4 / 16 h / Heating 5: 88.5 percent / thionyl chloride, pyridine / CH2Cl2 / 0.08 h / 0 °C 6: 90.6 percent / 1N KOH / methanol / 4 h / Ambient temperature 7: 27.4 percent / chromium trioxide-pyridine complex / 1 h / Ambient temperature 8: 39.1 percent / pyridine / 2.5 h / Heating View Scheme

1: 19.3 percent / HCO2H / CH2Cl2 / 2.5 h / 0 °C / various acid catalysts 2: 46.2 percent / 30percent H2O2 / methanol / 0.17 h / 0 °C 3: 93 percent / CCl4 / 16 h / Heating 4: 88.5 percent / thionyl chloride, pyridine / CH2Cl2 / 0.08 h / 0 °C 5: 90.6 percent / 1N KOH / methanol / 4 h / Ambient temperature 6: 27.4 percent / chromium trioxide-pyridine complex / 1 h / Ambient temperature 7: 39.1 percent / pyridine / 2.5 h / Heating View Scheme

1.1: 77 percent / p-TsOH / toluene / Heating 2.1: Dibal-H / petroleum ether; hexane / 0.5 h / -60 - 20 °C 2.2: 92 percent / SiO2 / H2O; toluene / 1 h / -20 - 0 °C View Scheme

1: 1.) NaBH4 / 1.) ethanol, r.t., 15 min; 2.) ethanol, r.t., 1.5 h 2: 65 percent / trifluoroacetic acid / CH2Cl2 / 0.25 h / 0 °C 3: 46.2 percent / 30percent H2O2 / methanol / 0.17 h / 0 °C 4: 93 percent / CCl4 / 16 h / Heating 5: 88.5 percent / thionyl chloride, pyridine / CH2Cl2 / 0.08 h / 0 °C 6: 90.6 percent / 1N KOH / methanol / 4 h / Ambient temperature 7: 27.4 percent / chromium trioxide-pyridine complex / 1 h / Ambient temperature 8: 39.1 percent / pyridine / 2.5 h / Heating View Scheme

pyridine 2.5 h; Heating;

1.1: 88 percent / mCPBA / ethyl acetate / 20 °C 2.1: 93 percent / nBuLi; DIPA / tetrahydrofuran / 20 °C 3.1: 77 percent / p-TsOH / toluene / Heating 4.1: Dibal-H / petroleum ether; hexane / 0.5 h / -60 - 20 °C 4.2: 92 percent / SiO2 / H2O; toluene / 1 h / -20 - 0 °C View Scheme

1.1: 93 percent / nBuLi; DIPA / tetrahydrofuran / 20 °C 2.1: 77 percent / p-TsOH / toluene / Heating 3.1: Dibal-H / petroleum ether; hexane / 0.5 h / -60 - 20 °C 3.2: 92 percent / SiO2 / H2O; toluene / 1 h / -20 - 0 °C View Scheme

1: 1) lithium diisopropyl amide / 1) THF, a) -78 deg C, 100 min, b) 10 deg C, 60 min, 2) 40 min 2: KOH; ethanol / 4 h 3: nBu4NCN / 8 h / 75 °C 4: 45 percent / ozone, sodium bicarbonate / ethyl acetate / 8 h / 0 °C 5: 92 percent / NaBH4 / ethanol / 1.5 h / Ambient temperature 6: conc. HCl / CH2Cl2 / 31 h 7: AIBN, tri-n-butyltin hydride / toluene / 2 h / Heating 8: 93 percent / ozone / ethyl acetate / 0.5 h / -78 °C 9: SOCl2 / methanol / 2 h 10: 99 percent / NaBH4, CeCl3*7H2O / methanol / 0.08 h 11: 75 percent / p-toluenesulphonic acid / toluene / 30 h / Heating 12: 63 percent / DIBAL-H / benzene / 2.5 h / Ambient temperature View Scheme

1: 27 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 4 h / Heating 2: 63 percent / DIBAL-H / benzene / 2.5 h / Ambient temperature View Scheme