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

1: diisobutylaluminum hydride / toluene / 5 h / -78 °C 2: KF*2H2O / methanol / 0.33 h / 23 °C 3: CH3SO3H, 3 Angstroem molecular sieves / CH2Cl2 / 5 h / 23 °C 4: 72 percent / Et3N, DMAP / CH2Cl2 / 6 h / 23 °C 5: 89 percent / DMAP / CH2Cl2 / 13 h / 23 °C 6: 92 percent / i-Pr2NEt / CH2Cl2 / 0.33 h / 23 °C 7: 1.) Bu3SnH, PdCl2(PPh3)2, HOAc, 2.) NaBH3CN, HOAc / 1.) CH2Cl2, 23 deg C, 15 min, 2.) CH3CN, 23 deg C, 30 min 8: 83 percent / PdCl2(PPh3)2, LiCl / dimethylformamide / 2 h / 80 °C 9: (PhSeO)2O / CH2Cl2 / 0.25 h / 23 °C 10: Bu4NF / tetrahydrofuran / 0.17 h / 23 °C 11: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / CH2Cl2 / 0.5 h / 23 °C 12: 0.5 h / -40 °C 13: 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 14: 23 °C 15: 84 percent / PdCl2(PPh3)2, Bu3SnH, HOAc / CH2Cl2 / 0.08 h / 23 °C 16: 70 percent / <N-methylpyridinium-4-carboxaldehyde>iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH2Cl2 / 0.67 h / 23 °C 17: 82 percent / silica gel / ethanol / 23 °C 18: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C 19: aq. AgNO3 / acetonitrile / 11 h / 23 °C View Scheme

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

1: Bu4NF / tetrahydrofuran / 0.17 h / 23 °C 2: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / CH2Cl2 / 0.5 h / 23 °C 3: 0.5 h / -40 °C 4: 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 5: 23 °C 6: 84 percent / PdCl2(PPh3)2, Bu3SnH, HOAc / CH2Cl2 / 0.08 h / 23 °C 7: 70 percent / <N-methylpyridinium-4-carboxaldehyde>iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH2Cl2 / 0.67 h / 23 °C 8: 82 percent / silica gel / ethanol / 23 °C 9: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C 10: aq. AgNO3 / acetonitrile / 11 h / 23 °C View Scheme

1: 84 percent / PdCl2(PPh3)2, Bu3SnH, HOAc / CH2Cl2 / 0.08 h / 23 °C 2: 70 percent / <N-methylpyridinium-4-carboxaldehyde>iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH2Cl2 / 0.67 h / 23 °C 3: 82 percent / silica gel / ethanol / 23 °C 4: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C 5: aq. AgNO3 / acetonitrile / 11 h / 23 °C View Scheme

1: 0.5 h / -40 °C 2: 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 3: 23 °C 4: 84 percent / PdCl2(PPh3)2, Bu3SnH, HOAc / CH2Cl2 / 0.08 h / 23 °C 5: 70 percent / <N-methylpyridinium-4-carboxaldehyde>iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH2Cl2 / 0.67 h / 23 °C 6: 82 percent / silica gel / ethanol / 23 °C 7: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C 8: aq. AgNO3 / acetonitrile / 11 h / 23 °C View Scheme

1: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C 2: aq. AgNO3 / acetonitrile / 11 h / 23 °C View Scheme

1: 83 percent / PdCl2(PPh3)2, LiCl / dimethylformamide / 2 h / 80 °C 2: (PhSeO)2O / CH2Cl2 / 0.25 h / 23 °C 3: Bu4NF / tetrahydrofuran / 0.17 h / 23 °C 4: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / CH2Cl2 / 0.5 h / 23 °C 5: 0.5 h / -40 °C 6: 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 7: 23 °C 8: 84 percent / PdCl2(PPh3)2, Bu3SnH, HOAc / CH2Cl2 / 0.08 h / 23 °C 9: 70 percent / <N-methylpyridinium-4-carboxaldehyde>iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH2Cl2 / 0.67 h / 23 °C 10: 82 percent / silica gel / ethanol / 23 °C 11: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C 12: aq. AgNO3 / acetonitrile / 11 h / 23 °C View Scheme

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

1: 1.) Bu3SnH, PdCl2(PPh3)2, HOAc, 2.) NaBH3CN, HOAc / 1.) CH2Cl2, 23 deg C, 15 min, 2.) CH3CN, 23 deg C, 30 min 2: 83 percent / PdCl2(PPh3)2, LiCl / dimethylformamide / 2 h / 80 °C 3: (PhSeO)2O / CH2Cl2 / 0.25 h / 23 °C 4: Bu4NF / tetrahydrofuran / 0.17 h / 23 °C 5: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / CH2Cl2 / 0.5 h / 23 °C 6: 0.5 h / -40 °C 7: 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 8: 23 °C 9: 84 percent / PdCl2(PPh3)2, Bu3SnH, HOAc / CH2Cl2 / 0.08 h / 23 °C 10: 70 percent / <N-methylpyridinium-4-carboxaldehyde>iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH2Cl2 / 0.67 h / 23 °C 11: 82 percent / silica gel / ethanol / 23 °C 12: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C 13: aq. AgNO3 / acetonitrile / 11 h / 23 °C View Scheme