1: 92 percent / nBuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 2: 49 percent / 1.) DIBALH / hexane; tetrahydrofuran / 1.) 50 deg C, 2 h; 2.) -20 deg C, 10 min; RT, 30 min 3: 92 percent / p-toluenesulfonic acid / CH2Cl2; methanol / 2 h / Ambient temperature 4: 90 percent / Dess-Martin's periodinane / CH2Cl2 / 0.5 h / Ambient temperature 5: 51 percent / nBuLi / diethyl ether; hexane / 1.) 0 deg C, 10 min; 2.) -42 deg C, 135 min 6: 6percent Na(Hg) / methanol; tetrahydrofuran / 3.5 h / -35 °C 7: LiOH / tetrahydrofuran; H2O / 18 h / Ambient temperature 8: Li/NH3(l) / ethanol / 0.5 h / -78 °C View Scheme