tetrabutyl ammonium fluoride in tetrahydrofuran Ambient temperature;

tetrabutyl ammonium fluoride in tetrahydrofuran

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: 93 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 8: 83 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: 93 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 3: 83 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: 93 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 7: 83 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: 93 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 6: 83 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: 93 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 5: 83 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: 93 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 2: 83 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

T=50°C; 2 h; Escherichia coli JA-300 cells, pH 6.5;

ammonia 1.) acetonitrile, irradiation, 36 h, 2.) methanol, room temperature, 24 h; Yield given. Multistep reaction. Yields of byproduct given;