1: 76 percent / N-bromosuccinimide / CCl4 / 1.3 h 2: 1.) NaBH4, 2.) p-TsOH / 1.) i-PrOH, 2.) acetone, reflux, 2 h 3: 64 percent / PCC / CH2Cl2 / 11 h / Heating 4: 88 percent / dimethylformamide / 15 h / 25 °C 5: 99 percent / diethyl ether; ethyl acetate / 15 h / 0 °C 6: 62 percent / (i-Bu)2AlH / CH2Cl2 / 3 h / 0 °C 7: PCC, NaOAc / CH2Cl2 / 13 h / 25 °C 8: NaN3 / LiCl / dimethylformamide / 15 h / 25 °C 9: 94 percent / diethyl ether / 3 h / 25 °C 10: 2.) NaBH3CN / 1.) Et2O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h 11: NaBH4 / methanol; H2O / 3 h / 0 °C 12: 50percent aq. TFA / 0.33 h / 0 °C View Scheme