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

ammonia; lithium; ammonium chloride in tetrahydrofuran T=-75°C; 0.0833333 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;