tetrabutyl ammonium fluoride in tetrahydrofuran Ambient temperature;

1: 0.49 g / tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / 0.42 h 2: 0.28 g / methanolic ammonia / 25 h / Ambient temperature View Scheme

1: 53 percent / tributyltin hydride, AIBN / benzene / 0.33 h / Heating 2: 0.49 g / tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / 0.42 h 3: 0.28 g / methanolic ammonia / 25 h / Ambient temperature View Scheme

1: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature 2: 1) lithium hexamethyldisilazide / 1) THF, -78 deg C, 1h, 2) room temperature, 30 min 3: tetrahydrofuran / -78 °C 4: DIBAL-H / toluene / 2 h / -78 °C 5: 96 percent / pyridine, DMAP / CH2Cl2 / 2 h / 0 °C 6: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h 7: 85.5 percent / methanol; H2O / 18 h / 85 °C 8: 96.5 percent / 30percent aq. H2O2, pyridine / CH2Cl2 / Ambient temperature 9: 90 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h 2: 85.5 percent / methanol; H2O / 18 h / 85 °C 3: 96.5 percent / 30percent aq. H2O2, pyridine / CH2Cl2 / Ambient temperature 4: 90 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: 1) lithium hexamethyldisilazide / 1) THF, -78 deg C, 1h, 2) room temperature, 30 min 2: tetrahydrofuran / -78 °C 3: DIBAL-H / toluene / 2 h / -78 °C 4: 96 percent / pyridine, DMAP / CH2Cl2 / 2 h / 0 °C 5: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h 6: 85.5 percent / methanol; H2O / 18 h / 85 °C 7: 96.5 percent / 30percent aq. H2O2, pyridine / CH2Cl2 / Ambient temperature 8: 90 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: tetrahydrofuran / -78 °C 2: DIBAL-H / toluene / 2 h / -78 °C 3: 96 percent / pyridine, DMAP / CH2Cl2 / 2 h / 0 °C 4: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h 5: 85.5 percent / methanol; H2O / 18 h / 85 °C 6: 96.5 percent / 30percent aq. H2O2, pyridine / CH2Cl2 / Ambient temperature 7: 90 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: DIBAL-H / toluene / 2 h / -78 °C 2: 96 percent / pyridine, DMAP / CH2Cl2 / 2 h / 0 °C 3: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h 4: 85.5 percent / methanol; H2O / 18 h / 85 °C 5: 96.5 percent / 30percent aq. H2O2, pyridine / CH2Cl2 / Ambient temperature 6: 90 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: 85.5 percent / methanol; H2O / 18 h / 85 °C 2: 96.5 percent / 30percent aq. H2O2, pyridine / CH2Cl2 / Ambient temperature 3: 90 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: 96.5 percent / 30percent aq. H2O2, pyridine / CH2Cl2 / Ambient temperature 2: 90 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme