1: KF*2H2O / methanol / 0.33 h / 23 °C 2: CH3SO3H, 3 Angstroem molecular sieves / CH2Cl2 / 5 h / 23 °C 3: 72 percent / Et3N, DMAP / CH2Cl2 / 6 h / 23 °C 4: 89 percent / DMAP / CH2Cl2 / 13 h / 23 °C 5: 92 percent / i-Pr2NEt / CH2Cl2 / 0.33 h / 23 °C 6: 1.) Bu3SnH, PdCl2(PPh3)2, HOAc, 2.) NaBH3CN, HOAc / 1.) CH2Cl2, 23 deg C, 15 min, 2.) CH3CN, 23 deg C, 30 min 7: 83 percent / PdCl2(PPh3)2, LiCl / dimethylformamide / 2 h / 80 °C 8: (PhSeO)2O / CH2Cl2 / 0.25 h / 23 °C 9: Bu4NF / tetrahydrofuran / 0.17 h / 23 °C 10: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / CH2Cl2 / 0.5 h / 23 °C 11: 0.5 h / -40 °C 12: 1.) i-Pr2NEt, 2.) tert-butyl alcohol, N-tert-butyl-N',N',N'',N''-tetramethylguanidine / 1.) 0 deg C, 30 min, 2.) 23 deg C 13: 23 °C 14: 84 percent / PdCl2(PPh3)2, Bu3SnH, HOAc / CH2Cl2 / 0.08 h / 23 °C 15: 70 percent / <N-methylpyridinium-4-carboxaldehyde>iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH2Cl2 / 0.67 h / 23 °C 16: 82 percent / silica gel / ethanol / 23 °C 17: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C 18: aq. AgNO3 / acetonitrile / 11 h / 23 °C View Scheme