1: 90 percent / aq. K2CO3 / CH2Cl2 / 0.5 h / 20 °C 2: 93 percent / Dowex 50W-X8 / aq. methanol / 18 h / 20 °C 3: 99 percent / imidazole / CH2Cl2 / 1 h / 20 °C 4: 92 percent / Et3N / tetrahydrofuran / 0.33 h / 20 °C 5: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 6: 65 percent / NaOAc; H2 / Pd/C / methanol / 6 h / 60 °C 7: 92 percent / Dowex 50W-X8; H2O / tetrahydrofuran / Heating View Scheme

1: 93 percent / Dowex 50W-X8 / aq. methanol / 18 h / 20 °C 2: 99 percent / imidazole / CH2Cl2 / 1 h / 20 °C 3: 92 percent / Et3N / tetrahydrofuran / 0.33 h / 20 °C 4: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 5: 65 percent / NaOAc; H2 / Pd/C / methanol / 6 h / 60 °C 6: 92 percent / Dowex 50W-X8; H2O / tetrahydrofuran / Heating View Scheme

1: 99 percent / imidazole / CH2Cl2 / 1 h / 20 °C 2: 92 percent / Et3N / tetrahydrofuran / 0.33 h / 20 °C 3: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4: 65 percent / NaOAc; H2 / Pd/C / methanol / 6 h / 60 °C 5: 92 percent / Dowex 50W-X8; H2O / tetrahydrofuran / Heating View Scheme

1.1: 98 percent / imidazole / dimethylformamide / 6 h / 20 °C 2.1: O3 / methanol / -78 °C 2.2: Me2S / methanol / 12 h / -78 - 20 °C 3.1: 1.01 g / H2 / Pd(OH)2/C / ethanol / 10 h / 20 °C 4.1: 90 percent / aq. K2CO3 / CH2Cl2 / 0.5 h / 20 °C 5.1: 93 percent / Dowex 50W-X8 / aq. methanol / 18 h / 20 °C 6.1: 99 percent / imidazole / CH2Cl2 / 1 h / 20 °C 7.1: 92 percent / Et3N / tetrahydrofuran / 0.33 h / 20 °C 8.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 9.1: 65 percent / NaOAc; H2 / Pd/C / methanol / 6 h / 60 °C 10.1: 92 percent / Dowex 50W-X8; H2O / tetrahydrofuran / Heating View Scheme

1: 92 percent / Et3N / tetrahydrofuran / 0.33 h / 20 °C 2: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 3: 65 percent / NaOAc; H2 / Pd/C / methanol / 6 h / 60 °C 4: 92 percent / Dowex 50W-X8; H2O / tetrahydrofuran / Heating View Scheme

1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 2: 65 percent / NaOAc; H2 / Pd/C / methanol / 6 h / 60 °C 3: 92 percent / Dowex 50W-X8; H2O / tetrahydrofuran / Heating View Scheme

1.1: O3 / methanol / -78 °C 1.2: Me2S / methanol / 12 h / -78 - 20 °C 2.1: 1.01 g / H2 / Pd(OH)2/C / ethanol / 10 h / 20 °C 3.1: 90 percent / aq. K2CO3 / CH2Cl2 / 0.5 h / 20 °C 4.1: 93 percent / Dowex 50W-X8 / aq. methanol / 18 h / 20 °C 5.1: 99 percent / imidazole / CH2Cl2 / 1 h / 20 °C 6.1: 92 percent / Et3N / tetrahydrofuran / 0.33 h / 20 °C 7.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 8.1: 65 percent / NaOAc; H2 / Pd/C / methanol / 6 h / 60 °C 9.1: 92 percent / Dowex 50W-X8; H2O / tetrahydrofuran / Heating View Scheme

1: 97 percent / p-toluenesulfonic acid / dimethylformamide 2: 93 percent / diisobutylaluminum hydride / CH2Cl2 / 0.5 h / -78 °C 3: 80 percent / Ti(Oi-Pr)4; (+)-diisopropyl tartrate; t-BuOOH / CH2Cl2 / -20 °C 4: 97 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 16 h / 20 °C 5: 92 percent / 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile / CH2Cl2; H2O / 3 h / 20 °C 6: 100 percent / diisopropylethylamine / CH2Cl2 / 20 °C 7: 91 percent / NaN3 / dimethylformamide / 80 °C 8: 83 percent / triphenylphosphine / tetrahydrofuran; H2O / 20 °C 9: 90 percent / ethanol / 65 h / Heating 10: 82 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran / 2 h / -78 °C 11: 97 percent / potassium carbonate / acetonitrile / 5 h / Heating 12: 100 percent / tetra-n-butylammonium fluoride dihydrate / tetrahydrofuran / 14 h / 20 °C 13: (COCl)2; triethylamine / dimethylsulfoxide; CH2Cl2 / -78 - 20 °C 14: 71 percent / TiCl4 / CH2Cl2 / 15 h / -78 °C 15: OsO4; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 16: 45 mg / NaHCO3; NaIO4 / tetrahydrofuran; H2O / 3 h / 20 °C 17: 81 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 24 h / 20 °C View Scheme

1: 80 percent / Ti(Oi-Pr)4; (+)-diisopropyl tartrate; t-BuOOH / CH2Cl2 / -20 °C 2: 97 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 16 h / 20 °C 3: 92 percent / 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile / CH2Cl2; H2O / 3 h / 20 °C 4: 100 percent / diisopropylethylamine / CH2Cl2 / 20 °C 5: 91 percent / NaN3 / dimethylformamide / 80 °C 6: 83 percent / triphenylphosphine / tetrahydrofuran; H2O / 20 °C 7: 90 percent / ethanol / 65 h / Heating 8: 82 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran / 2 h / -78 °C 9: 97 percent / potassium carbonate / acetonitrile / 5 h / Heating 10: 100 percent / tetra-n-butylammonium fluoride dihydrate / tetrahydrofuran / 14 h / 20 °C 11: (COCl)2; triethylamine / dimethylsulfoxide; CH2Cl2 / -78 - 20 °C 12: 71 percent / TiCl4 / CH2Cl2 / 15 h / -78 °C 13: OsO4; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 14: 45 mg / NaHCO3; NaIO4 / tetrahydrofuran; H2O / 3 h / 20 °C 15: 81 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 24 h / 20 °C View Scheme

1: 71 percent / TiCl4 / CH2Cl2 / 15 h / -78 °C 2: OsO4; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 3: 45 mg / NaHCO3; NaIO4 / tetrahydrofuran; H2O / 3 h / 20 °C 4: 81 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 24 h / 20 °C View Scheme