tetrabutyl ammonium fluoride in tetrahydrofuran 0.333333 h; Ambient temperature;

zinc dibromide in dichloromethane 18 h; Ambient temperature;

1: 9.9 g / sodium periodate / methanol; H2O / 20 h / Ambient temperature 2: 87 percent / NaBH4 / ethanol / 2 h / Ambient temperature 3: 77 percent / pyridine / 24 h / Ambient temperature 4: 73 percent / 80percent acetic acid / 6 h / 65 °C 5: 93 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature 6: 59 percent / t-BuOK / 2-methyl-propan-2-ol / 2.5 h / 60 °C 7: 79 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / Ambient temperature View Scheme

1: 77 percent / pyridine / 24 h / Ambient temperature 2: 73 percent / 80percent acetic acid / 6 h / 65 °C 3: 93 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature 4: 59 percent / t-BuOK / 2-methyl-propan-2-ol / 2.5 h / 60 °C 5: 79 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / Ambient temperature View Scheme

1: 87 percent / NaBH4 / ethanol / 2 h / Ambient temperature 2: 77 percent / pyridine / 24 h / Ambient temperature 3: 73 percent / 80percent acetic acid / 6 h / 65 °C 4: 93 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature 5: 59 percent / t-BuOK / 2-methyl-propan-2-ol / 2.5 h / 60 °C 6: 79 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / Ambient temperature View Scheme

1: 93 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature 2: 59 percent / t-BuOK / 2-methyl-propan-2-ol / 2.5 h / 60 °C 3: 79 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / Ambient temperature View Scheme

1: 59 percent / t-BuOK / 2-methyl-propan-2-ol / 2.5 h / 60 °C 2: 79 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / Ambient temperature View Scheme

1: 73 percent / 80percent acetic acid / 6 h / 65 °C 2: 93 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature 3: 59 percent / t-BuOK / 2-methyl-propan-2-ol / 2.5 h / 60 °C 4: 79 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / Ambient temperature View Scheme

1: 78 percent / pyridine / Ambient temperature 2: 65 percent / KO(t-Bu) / tetrahydrofuran / 100 h / 40 °C / 3 equiv. of KO(t-Bu) 3: 71 percent / ZnBr2 / CH2Cl2 / 18 h / Ambient temperature View Scheme