1.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 °C 2.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating 3.1: 3.3 mg / K2CO3; H2O / methanol / 20 °C 4.1: n-BuLi; oxygen / tetrahydrofuran; hexane / 0.25 h / -78 °C 4.2: 45 percent / NH4Cl; H2O; dimethylsulfide / tetrahydrofuran; hexane / 1 h / 20 °C 5.1: 59 percent / H2O / p-toluenesulfonic acid / CHCl3; methanol / 0.5 h / 0 °C View Scheme

1.1: aq. m-chloroperbenzoic acid / CH2Cl2 / 24 h / Heating 1.2: 63 percent / KOH / ethanol / 2 h / 20 °C 2.1: 90 percent / silver trifluoroacetate; Br2 / CHCl3 / 1 h / 10 - 15 °C 3.1: 94 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h 4.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 °C 4.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 °C 5.1: NaH / dimethylformamide / 0.5 h / -5 °C 5.2: dimethylformamide / 0.25 h / -5 °C 6.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C 7.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation 8.1: NaBH4 / ethanol / 16 h / 20 °C 9.1: 12.9 mg / aq. H2O2 / tetrahydrofuran; ethanol / 22 h / 20 °C 10.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 10.2: 94 percent / tetrahydrofuran / 20 h / 20 °C 11.1: pyridine; trimethylamine-N-oxide dihydrate; H2O / OsO4; acetone / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 °C 12.1: 19.2 mg / p-TsOH / 2 h / 20 °C 13.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 °C 14.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating 15.1: 3.3 mg / K2CO3; H2O / methanol / 20 °C 16.1: n-BuLi; oxygen / tetrahydrofuran; hexane / 0.25 h / -78 °C 16.2: 45 percent / NH4Cl; H2O; dimethylsulfide / tetrahydrofuran; hexane / 1 h / 20 °C 17.1: 59 percent / H2O / p-toluenesulfonic acid / CHCl3; methanol / 0.5 h / 0 °C View Scheme

1.1: 84 percent / K2CO3; CuO / dimethylformamide / 8 h / Heating 2.1: aq. m-chloroperbenzoic acid / CH2Cl2 / 24 h / Heating 2.2: 63 percent / KOH / ethanol / 2 h / 20 °C 3.1: 90 percent / silver trifluoroacetate; Br2 / CHCl3 / 1 h / 10 - 15 °C 4.1: 94 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h 5.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 °C 5.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 °C 6.1: NaH / dimethylformamide / 0.5 h / -5 °C 6.2: dimethylformamide / 0.25 h / -5 °C 7.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C 8.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation 9.1: NaBH4 / ethanol / 16 h / 20 °C 10.1: 12.9 mg / aq. H2O2 / tetrahydrofuran; ethanol / 22 h / 20 °C 11.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 11.2: 94 percent / tetrahydrofuran / 20 h / 20 °C 12.1: pyridine; trimethylamine-N-oxide dihydrate; H2O / OsO4; acetone / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 °C 13.1: 19.2 mg / p-TsOH / 2 h / 20 °C 14.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 °C 15.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating 16.1: 3.3 mg / K2CO3; H2O / methanol / 20 °C 17.1: n-BuLi; oxygen / tetrahydrofuran; hexane / 0.25 h / -78 °C 17.2: 45 percent / NH4Cl; H2O; dimethylsulfide / tetrahydrofuran; hexane / 1 h / 20 °C 18.1: 59 percent / H2O / p-toluenesulfonic acid / CHCl3; methanol / 0.5 h / 0 °C View Scheme

1.1: N-bromosuccinimide; azobis(isobutyronitrile) / benzene / 0.33 h / Heating 1.2: tri-n-butyltinhydride; azobis(isobutyronitrile) / benzene / 3.5 h / Heating 2.1: O2; Rose Bengal / acetone / 8 h / -10 °C / Irradiation 2.2: RuCl2(PPh3)3 / CH2Cl2 / -10 - 20 °C 2.3: 42 percent / NaOMe / methanol / 0.5 h / -5 °C 3.1: 99 percent / Et3N; 4-dimethylaminopyridine / CH2Cl2 / 0 - 20 °C 4.1: 80 percent Turnov. / cholesterol esterase; aq. NaOH / 36 h / 5 °C / pH 7.7 5.1: 98 percent / imidazole / dimethylformamide / 0.67 h / 20 °C 6.1: 81 percent Turnov. / LiOH*H2O / methanol / 48 h / -5 °C 7.1: diphenylphosphorazidate; Et3N / benzene / 1 h 7.2: toluene / 1 h / 110 °C 8.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 °C 8.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 °C 9.1: NaH / dimethylformamide / 0.5 h / -5 °C 9.2: dimethylformamide / 0.25 h / -5 °C 10.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C 11.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation 12.1: NaBH4 / ethanol / 16 h / 20 °C 13.1: 12.9 mg / aq. H2O2 / tetrahydrofuran; ethanol / 22 h / 20 °C 14.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 14.2: 94 percent / tetrahydrofuran / 20 h / 20 °C 15.1: pyridine; trimethylamine-N-oxide dihydrate; H2O / OsO4; acetone / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 °C 16.1: 19.2 mg / p-TsOH / 2 h / 20 °C 17.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 °C 18.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating 19.1: 3.3 mg / K2CO3; H2O / methanol / 20 °C 20.1: n-BuLi; oxygen / tetrahydrofuran; hexane / 0.25 h / -78 °C 20.2: 45 percent / NH4Cl; H2O; dimethylsulfide / tetrahydrofuran; hexane / 1 h / 20 °C 21.1: 59 percent / H2O / p-toluenesulfonic acid / CHCl3; methanol / 0.5 h / 0 °C View Scheme

1.1: 90 percent / silver trifluoroacetate; Br2 / CHCl3 / 1 h / 10 - 15 °C 2.1: 94 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h 3.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 °C 3.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 °C 4.1: NaH / dimethylformamide / 0.5 h / -5 °C 4.2: dimethylformamide / 0.25 h / -5 °C 5.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C 6.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation 7.1: NaBH4 / ethanol / 16 h / 20 °C 8.1: 12.9 mg / aq. H2O2 / tetrahydrofuran; ethanol / 22 h / 20 °C 9.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 9.2: 94 percent / tetrahydrofuran / 20 h / 20 °C 10.1: pyridine; trimethylamine-N-oxide dihydrate; H2O / OsO4; acetone / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 °C 11.1: 19.2 mg / p-TsOH / 2 h / 20 °C 12.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 °C 13.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating 14.1: 3.3 mg / K2CO3; H2O / methanol / 20 °C 15.1: n-BuLi; oxygen / tetrahydrofuran; hexane / 0.25 h / -78 °C 15.2: 45 percent / NH4Cl; H2O; dimethylsulfide / tetrahydrofuran; hexane / 1 h / 20 °C 16.1: 59 percent / H2O / p-toluenesulfonic acid / CHCl3; methanol / 0.5 h / 0 °C View Scheme

lithium chloride in N,N-dimethyl-formamide T=120°C; 4 h;

1: 46 percent / SmI2 / tetrahydrofuran / 144 h 2: 89 percent / trifluoroacetic acid / 0.17 h / 0 °C View Scheme

1: 96 percent / K2CO3 / dimethylformamide / 22 h 2: 38 percent / SmI2 / tetrahydrofuran / 44 h 3: 89 percent / trifluoroacetic acid / 0.17 h / 0 °C View Scheme

1: 38 percent / SmI2 / tetrahydrofuran / 44 h 2: 89 percent / trifluoroacetic acid / 0.17 h / 0 °C View Scheme

1: 87 percent / SmI2 / tetrahydrofuran; methanol / 2 h / 0 - 20 °C 2: 89 percent / trifluoroacetic acid / 0.17 h / 0 °C View Scheme