diisobutylaluminium hydride in diethyl ether T=0°C; 1 h;

hydrogen; P-2-nickel T=15°C;

1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 0 °C 2: n-BuLi / hexane; tetrahydrofuran / 2 h / 0 °C 3: 89 percent / DIBAL-H / diethyl ether / 1 h / 0 °C View Scheme

1: 82 percent / LiAlH4 / diethyl ether / 5 h / Heating 2: 84 percent / H2 / P-2-nickel / 15 °C View Scheme

1: n-BuLi / hexane; tetrahydrofuran / 2 h / 0 °C 2: 89 percent / DIBAL-H / diethyl ether / 1 h / 0 °C View Scheme

in diethyl ether T=-20°C;

1: 82 percent / (+)-DIPT, t-BuO2H, Ti(O-iPr)4 2: 88 percent / CCl4, PPh3 3: 79 percent 4: 78 percent / imidazole / dimethylformamide 5: 2) Et2NH, CuI / 1) Pd(PPh3)4 / 1) benzene, rt, 1 h, 2) 5 h 6: 91 percent / H2 / Lindlar catalyst / ethanol 7: 92 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature 8: 73 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme