1: 59 percent / NaOMe / methanol; CHCl3 / 120 h / 25 °C 2: 1.) CuCl / 1.) ether, THF, -30 deg C, 20 min, 2.) -30 deg C, 20 min; 0 deg C, 40 min 3: 81 percent / NaH / dimethylformamide / 4 h / 20 °C 4: 97 percent / n-Bu4NF / tetrahydrofuran / 2.5 h / 25 °C 5: DMSO, (COCl)2 / CH2Cl2 / -78 - 0 °C 6: n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C to -40 deg C, 2.) 20 deg C, 3 h 7: 1.) B2H6*THF, 2.) 3 N NaOH, 30percent H2O2 / 1.) THF, 15-20 deg C, 30 min, 2.) EtOH, 40 deg C, 30 min 8: 100 percent / i-Pr2NEt / CH2Cl2 / 1.) 25 deg C, 5 h, 2.) 40 deg C, 2.5 h 9: 99 percent / nBu4NF / tetrahydrofuran / 2.5 h / 25 °C 10: DMSO, (COCl)2 / CH2Cl2 / 0.5 h / -78 °C 11: t-BuOK / tetrahydrofuran / 1.) 25 deg C, 1.5 h, 2.) 55 deg C, 1 h 12: methanol / 2 h / 25 °C 13: NaBH4, AcOH / 2 h / 25 °C 14: 76 percent / Na, NH3 / tetrahydrofuran / 0.25 h / -78 °C 15: 96 percent / pyridine, DMAP / 0.5 h / 0 °C 16: 42 percent / KI, ZnCu / dimethylformamide / 4 h / Heating 17: aq. acetic acid / 0.5 h / 40 °C 18: Jones reagent / acetone / 1 h / 25 °C 19: 100 percent / 80percent aq. AcOH / 3 h / Heating View Scheme