diisobutylaluminium hydride in dichloromethane T=0°C; Yield given;

1: 79 percent / CF3SO3H / CH2Cl2; cyclohexane / Ambient temperature 2: 1) aq. KOH, 2) I2, KI, 3) 1,4-diazabicyclo<2.2.2>octane / 1) MeOH, r.t., 2) H2O, hexane, EtOAc, r.t., 1 h, 3) DMSO, 132-140 deg C, 15 min 3: diisobutylaluminium hydride / CH2Cl2 / 0 °C View Scheme

1: 1) KOtBu / 1) THF, 1 h, r.t., 2) THF, r.t., 1 h 2: 92 percent / 48 h / 130 °C 3: 1) disiamylborane, BH3*SMe2, 2) 30percent H2O2 / 1) THF, r.t., 30 min, 2) MeOH 4: 84 percent / (COCl)2, DMSO / CH2Cl2 / 0.05 h / -30 °C 5: Me2AlCl, MeOH / CH2Cl2; hexane / 0.5 h / -40 deg C to r.t. 6: 99.4 percent / tetrahydrofuran / 2 h / Ambient temperature 7: 64 percent / NH3 liq., Li / tetrahydrofuran / 1 h 8: 1) KOtBu / 1) THF, r.t., 1 h, 2) THF, r.t., 15 min 9: Bu4NF / tetrahydrofuran / 3 h / Ambient temperature 10: pyridine, 4-(N,N-dimethylamino)pyridine / Ambient temperature 11: 87 percent / p-TsOH, H2O / acetone / 2 h / 56 °C 13: 66 percent / Et3N / 20 h / Ambient temperature 14: 1) s-Bu3BHLi, 2) H2O2 / 1) THF, -78 deg C, 30 min, 2) THF, H2O, to r.t. 15: KOH / methanol / 2 h / 60 °C 16: 99 percent / imidazole / dimethylformamide / 3 h / 80 °C 17: VO(acac)2, tert-butylhydroperoxide / CH2Cl2 / 3 h / 0 °C 18: 89 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 48 h / Ambient temperature 19: 67 percent / CrO3, AcOH / CH2Cl2; H2O / 2 h 20: 1) 2,6-lutidine, trimethylsilyl trifluoromethanesulfonate, 2) Bu4NF, AcOH / 1) CH2Cl2, -60 deg C to 10 deg C, 2 h, 2) THF, 30 min 21: 86 percent / N,N-diethyl-N<<(methoxycarbonyl)amino>sulfonyl>ethanaminium hydroxide / benzene / 0.25 h / 80 °C 22: 85 percent / Bu4NF, AcOH / tetrahydrofuran; H2O / 29 h View Scheme