tetrabutyl ammonium fluoride in tetrahydrofuran 1.) 0 deg C, 1 h, 2.) room temperature, 3 h;

lithium amide in hexane; ammonia 0.5 h;

1: 80 percent / KHMDS, 18-crown-6 / tetrahydrofuran / -78 °C 2: 95 percent / DIBALH / tetrahydrofuran / -40 - 0 °C 3: 95 percent / NCS, DMS / CH2Cl2 / -40 - 0 °C 4: tetrahydrofuran / -78 °C 5: 82 percent / TBAF / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h View Scheme

1: 95 percent / NCS, DMS / CH2Cl2 / -40 - 0 °C 2: tetrahydrofuran / -78 °C 3: 82 percent / TBAF / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h View Scheme

1: H2 / Ph3RhCl / benzene / 760 Torr 2: 82 percent / TBAF / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h View Scheme

1: 95 percent / tetrahydrofuran / 0 °C 2: H2 / Ph3RhCl / benzene / 760 Torr 3: 82 percent / TBAF / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h View Scheme

1: 93 percent / aluminium isopropoxide / toluene / 8 h / Heating 2: 78 percent / t-BuOOH / 2.) VO(acac)2 / benzene / 4 h / Ambient temperature 3: 63 percent / copper(I) iodide / diethyl ether / 4 h / 0 °C 4: 1.) N,N-dimethylformamide dimethyl acetale / 1.) rt., overnight; 2.) acetic anhydride, boiling, 8 h 5: 84 percent / LiNH2 / liquid ammonia; hexane / 0.5 h View Scheme

1: 78 percent / t-BuOOH / 2.) VO(acac)2 / benzene / 4 h / Ambient temperature 2: 63 percent / copper(I) iodide / diethyl ether / 4 h / 0 °C 3: 1.) N,N-dimethylformamide dimethyl acetale / 1.) rt., overnight; 2.) acetic anhydride, boiling, 8 h 4: 84 percent / LiNH2 / liquid ammonia; hexane / 0.5 h View Scheme

1: 69 percent / 3-chloro peroxybenzoic acid / CH2Cl2 / 1 h / 0 °C 2: 93 percent / aluminium isopropoxide / toluene / 8 h / Heating 3: 78 percent / t-BuOOH / 2.) VO(acac)2 / benzene / 4 h / Ambient temperature 4: 63 percent / copper(I) iodide / diethyl ether / 4 h / 0 °C 5: 1.) N,N-dimethylformamide dimethyl acetale / 1.) rt., overnight; 2.) acetic anhydride, boiling, 8 h 6: 84 percent / LiNH2 / liquid ammonia; hexane / 0.5 h View Scheme

1: tetrahydrofuran / -78 °C 2: 82 percent / TBAF / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h View Scheme