1: 83 percent / 10percent KOH / tetrahydrofuran; ethanol; H2O / 84 h / Ambient temperature 2: 100 percent / B2H6*THF / Ambient temperature 3: 96 percent / Dess-Martin periodinane / CH2Cl2 / Ambient temperature 4: 98 percent / Ph3P / CH2Cl2 / 0.5 h / 0 °C 5: 90 percent / DIBALH / toluene; hexane / 1.) -78 deg C, 10 min; 2.) 0 deg C, 30 min 6: 90 percent / Et3N, DMAP / dimethylformamide / 72 h / Ambient temperature 7: 92 percent / nBuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 8: 49 percent / 1.) DIBALH / hexane; tetrahydrofuran / 1.) 50 deg C, 2 h; 2.) -20 deg C, 10 min; RT, 30 min 9: 92 percent / p-toluenesulfonic acid / CH2Cl2; methanol / 2 h / Ambient temperature 10: 90 percent / Dess-Martin's periodinane / CH2Cl2 / 0.5 h / Ambient temperature 11: 51 percent / nBuLi / diethyl ether; hexane / 1.) 0 deg C, 10 min; 2.) -42 deg C, 135 min 12: 6percent Na(Hg) / methanol; tetrahydrofuran / 3.5 h / -35 °C 13: LiOH / tetrahydrofuran; H2O / 18 h / Ambient temperature 14: Li/NH3(l) / ethanol / 0.5 h / -78 °C View Scheme