diisobutylaluminium hydride in diethyl ether; toluene T=0 - 20°C; 17 h;

diisobutylaluminium hydride in toluene T=-78°C; 0.5 h;

1: 89 percent / DIBAH / toluene / 0.5 h / -78 °C 2: 84 percent 3: 93 percent / CrO3-pyridine / CH2Cl2 / 15 h / Ambient temperature 4: 38 percent / p-toluenesulfonic acid monohydrate / benzene / 4 h / Heating 5: 1.) ozone, 2.) dimethyl sulfide / 1a.) CH2Cl2, -78 deg C, 1 h, 1b.) RT, 0.5 h, 2.) RT, 1 h 6: 1.) sodium hydride / 1.) THF, 15 min, 2.) RT, 4 h 7: 98 percent / H2 / 10percent Pd/C / ethyl acetate / 0.5 h / 2068.6 Torr / Ambient temperature 8: 90 percent / DIBAH / toluene / 0.5 h / -78 °C 11: 79 percent / N,N-diisopropylethylamine / CH2Cl2 / 19 h / Ambient temperature 12: 1.) ozone, 2.) Me2S / 1a.) CH2Cl2, -78 deg C, 0.5 h, 1b.) RT, O.5 h, 2.) RT, 1 h 13: pyridinium dichromate / dimethylformamide / 17 h / Ambient temperature 14: dimethylformamide; H2O; diethyl ether / 1 h / Ambient temperature 15: 72 percent / ZnBr2 / CH2Cl2 / 3 h / Ambient temperature 16: 96 percent / aq. NaOH / propan-2-ol / 0.5 h / 60 °C 17: 48 percent / benzenesulfonyl chloride, pyridine 18: 44 percent / Zn, dibromoethane / tetrahydrofuran / 1.12 h / Heating 19: 30 percent / SOCl2, pyridine / CH2Cl2 / 0.08 h / Heating 20: 76 percent / 50percent aq. HF / tetrahydrofuran / 18 h / Ambient temperature View Scheme