ammonium cerium(IV) nitrate in acetone 0°C, 2 h;

tetrabutyl ammonium fluoride in tetrahydrofuran Reduction; 1.5 h;

1.1: 95 percent / Br2 / CCl4 / 2 h / Heating 2.1: 95 percent / NaHCO3 / acetone / 12 h / Heating 3.1: 88 percent / PdCl2(PPh3)2; Et2NH; CuI / 3 h / 0 °C 4.1: DIBAL-H / hexane / 50 h / 20 °C 4.2: NBS / 6 h / -20 °C 5.1: t-BuLi / diethyl ether / -80 - -20 °C 5.2: 29 percent / (PhSO2)2S / diethyl ether / 6.5 h / -80 - 20 °C 6.1: 26 percent / aq. TBAF / tetrahydrofuran / 1.5 h View Scheme

1.1: 88 percent / PdCl2(PPh3)2; Et2NH; CuI / 3 h / 0 °C 2.1: DIBAL-H / hexane / 50 h / 20 °C 2.2: NBS / 6 h / -20 °C 3.1: t-BuLi / diethyl ether / -80 - -20 °C 3.2: 29 percent / (PhSO2)2S / diethyl ether / 6.5 h / -80 - 20 °C 4.1: 26 percent / aq. TBAF / tetrahydrofuran / 1.5 h View Scheme

1.1: DIBAL-H / hexane / 50 h / 20 °C 1.2: NBS / 6 h / -20 °C 2.1: t-BuLi / diethyl ether / -80 - -20 °C 2.2: 29 percent / (PhSO2)2S / diethyl ether / 6.5 h / -80 - 20 °C 3.1: 26 percent / aq. TBAF / tetrahydrofuran / 1.5 h View Scheme

1.1: t-BuLi / diethyl ether / -80 - -20 °C 1.2: 29 percent / (PhSO2)2S / diethyl ether / 6.5 h / -80 - 20 °C 2.1: 26 percent / aq. TBAF / tetrahydrofuran / 1.5 h View Scheme

1: 95 percent / 0.4M CeCl3*7H2O, Na-boranate / methanol / 0.17 h / Ambient temperature View Scheme

3-chloro-benzenecarboperoxoic acid in dichloromethane T=-25°C; 20 h;