1: 54 percent / tetrahydrofuran / 2 h / -90 - -80 °C 2: 1.) L-Selectride, 2.) 30percent hydrogen peroxide, 3 N sodium hydroxide, 3.) p-toluenesulfonic acid 3: 67 percent / silver oxide / acetonitrile / 46 h / Heating 4: 98 percent / lithium diisopropylamide / tetrahydrofuran 5: 89 percent / diisobutylaluminium hydride / toluene / 2.5 h / -110 °C 6: 89 percent / tetrahydrofuran / -35 °C 7: 100 percent / acetic acid / H2O / 4 h / Ambient temperature 8: 98 percent / lithium hydroxide monohydrate / H2O; methanol / 24 h / 25 °C 9: triethylamine / CH2Cl2 / 2 h 10: 51 percent / xylene / 11 h / Heating 11: 72 percent / N-chlorosuccinimide, silver nitrate / acetonitrile; H2O / 1.) -5 deg C, 0.5 h, 2.) room temperature, 1 h 12: 95 percent / sodium borohydride / methanol / 0.75 h / -110 °C 13: acetonitrile; pentane / 15 h / Ambient temperature 14: 16.1 mg / anhydrous sodium iodide, chlorotrimethylsilane / acetonitrile / 3.25 h View Scheme