1: 99 percent / quinoline, hydrogen / Pd/BaSO4 / 50 h 2: 92 percent / 4-(dimethylamino)pyridine / pyridine / 7 h / 60 °C / Heating 3: 95 percent / m-PCBA / CH2Cl2 / 1 h / 0 °C 4: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature 5: 85 percent / ozone, dimethyl sulfide / CH2Cl2 / 18 h / 40 °C / Heating 6: 91 percent / DBU / CH2Cl2 / 1 h / Ambient temperature 7: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C 8: 85 percent / HCl / methanol / 15 h / 0 °C 9: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min 10: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C 11: 96 percent / DMAP / pyridine / 3.33 h / 50 °C 12: 96 percent / KOH / methanol / 8.5 h / Ambient temperature 13: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min 14: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature 15: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min 16: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature 17: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature View Scheme