1: 72 percent / HCl, H2 / 5percent Pd/C / methanol / 5 h / Ambient temperature 2: 98 percent / p-toluenesulfonic acid / 10 h / Heating 3: 1.) O3, 2.) LiOH / 1.) CH2Cl2, -78 deg C, 30 min, 2.) THF, RT, 2 h 4: 73 percent / camphorsulfonic acid / benzene / 2 h / Heating 5: 72 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 6: 93 percent / 4-(dimethylamino)pyridine, pyridine / 5 h / Ambient temperature 7: 95 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 8: 95 percent / HCl / acetone / 6 h / Ambient temperature 9: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, 0 deg C, 30 min 10: 50 percent / LDA / tetrahydrofuran / 0.17 h / -78 °C 11: pyridine / 1 h / 0 °C 12: 1.) LiBr, Li2CO3, DMF, 2.) H2 / 2.) 5percent Pd/C / 1.) 150 deg C, 4 h, 2.) ethyl acetate, RT, 8 h 14: 5percent sodium amalgam / tetrahydrofuran; methanol / 9 h / -20 - 20 °C 15: n-Bu4NF / tetrahydrofuran / 2 h / Ambient temperature View Scheme