1: NaHCO3 / H2O; tetrahydrofuran / Ambient temperature 2: 73 percent / MnO2 / toluene / 5 h / Heating 3: 70 percent / diethylamino-sulfur trifluoride / CH2Cl2 / Ambient temperature 4: 58 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.67 h / Ambient temperature View Scheme

1: 84 percent / NaBH4 / dimethylformamide / 20 °C 2: 95 percent / TBAF*3H2O / tetrahydrofuran / 1 h / 20 °C 3: glutathione; O2 / 3 h / 37 °C View Scheme

1: 84 percent / NaBH4 / dimethylformamide / 20 °C 2: 95 percent / TBAF*3H2O / tetrahydrofuran / 1 h / 20 °C 3: glutathione; O2 / 3 h / 37 °C View Scheme

With  sodium hydrogencarbonate in  tetrahydrofuran; water  Ambient temperature;  Yield given;   

Multi-step reaction with 2 steps 1: NaHCO3 / H2O; tetrahydrofuran / Ambient temperature2: 73 percent / MnO2 / toluene / 5 h / Heating  

With  N-bromosuccinmide; dibenzoyl peroxide in  tetrachloromethane 1 h;  Heating;   

Multi-step reaction with 3 steps 1: NaHCO3 / H2O; tetrahydrofuran / Ambient temperature2: 73 percent / MnO2 / toluene / 5 h / Heating3: 70 percent / diethylamino-sulfur trifluoride / CH2Cl2 / Ambient temperature