1: 1.) rose bengal, bis(triethyl ammonium) salt, oxygen, 2.) lithium tris-tert-butoxyaluminohydride / 1.) CCl4, methanol, 20 min, irrad., 2.) THF, -78 deg C, 20 min 2: 1.) BH3*DMS, 2.) 6 M HCl / 1a.) THF, RT, 20 min, 1b.) reflux, 30 min, 2.) reflux, 30 min 3: 82 percent / H2, conc. aq. HCl / 10percent Pd/C / methanol / 6 h / 2585.7 Torr View Scheme

1: 1.) triethylaluminum / 1.) CH2Cl2, hexane, 30 min, 2.) CH2Cl2, r.t., 14 h 2: 88 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C 3: 85 percent / N,N-diisopropylethylamine / CHCl3 / 1 h / Heating 4: 91 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 5: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -80 deg C, 2 h, 2.) -80 deg C to r.t. 6: 45 percent / TiCl4, molecular sieves 4A / CH2Cl2 / 0.5 h / -80 °C 7: 81 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 8: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature 9: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating 10: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 11: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 12: 80 percent / pyridine / 14 h / Ambient temperature 13: 1.) H2, 2.) Et3N / 1.) Pd(OH)2 / 1.) MeOH, 1 atm, 1 h, 2.) reflux, 1.5 h 14: 71 percent / a) conc. HCl, b) Dowex 1-X8, OH(1-)-form / a) MeOH, reflux, 30 min, b) H2O View Scheme

1: 88 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C 2: 85 percent / N,N-diisopropylethylamine / CHCl3 / 1 h / Heating 3: 91 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 4: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -80 deg C, 2 h, 2.) -80 deg C to r.t. 5: 45 percent / TiCl4, molecular sieves 4A / CH2Cl2 / 0.5 h / -80 °C 6: 81 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 7: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature 8: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating 9: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 10: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 11: 80 percent / pyridine / 14 h / Ambient temperature 12: 1.) H2, 2.) Et3N / 1.) Pd(OH)2 / 1.) MeOH, 1 atm, 1 h, 2.) reflux, 1.5 h 13: 71 percent / a) conc. HCl, b) Dowex 1-X8, OH(1-)-form / a) MeOH, reflux, 30 min, b) H2O View Scheme

1: 85 percent / N,N-diisopropylethylamine / CHCl3 / 1 h / Heating 2: 91 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -80 deg C, 2 h, 2.) -80 deg C to r.t. 4: 45 percent / TiCl4, molecular sieves 4A / CH2Cl2 / 0.5 h / -80 °C 5: 81 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 6: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature 7: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating 8: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 9: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 10: 80 percent / pyridine / 14 h / Ambient temperature 11: 1.) H2, 2.) Et3N / 1.) Pd(OH)2 / 1.) MeOH, 1 atm, 1 h, 2.) reflux, 1.5 h 12: 71 percent / a) conc. HCl, b) Dowex 1-X8, OH(1-)-form / a) MeOH, reflux, 30 min, b) H2O View Scheme

1: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -80 deg C, 2 h, 2.) -80 deg C to r.t. 2: 45 percent / TiCl4, molecular sieves 4A / CH2Cl2 / 0.5 h / -80 °C 3: 81 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 4: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature 5: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating 6: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 7: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 8: 80 percent / pyridine / 14 h / Ambient temperature 9: 1.) H2, 2.) Et3N / 1.) Pd(OH)2 / 1.) MeOH, 1 atm, 1 h, 2.) reflux, 1.5 h 10: 71 percent / a) conc. HCl, b) Dowex 1-X8, OH(1-)-form / a) MeOH, reflux, 30 min, b) H2O View Scheme

1: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -80 deg C, 30 min, 2.) THF, -80 deg C, 20 min 2: 81 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 3: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature 4: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating 5: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 6: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 7: 80 percent / pyridine / 14 h / Ambient temperature 8: 1.) H2, 2.) Et3N / 1.) Pd(OH)2 / 1.) MeOH, 1 atm, 1 h, 2.) reflux, 1.5 h 9: 71 percent / a) conc. HCl, b) Dowex 1-X8, OH(1-)-form / a) MeOH, reflux, 30 min, b) H2O View Scheme

1: 91 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -80 deg C, 2 h, 2.) -80 deg C to r.t. 3: 45 percent / TiCl4, molecular sieves 4A / CH2Cl2 / 0.5 h / -80 °C 4: 81 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 5: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature 6: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating 7: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 8: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 9: 80 percent / pyridine / 14 h / Ambient temperature 10: 1.) H2, 2.) Et3N / 1.) Pd(OH)2 / 1.) MeOH, 1 atm, 1 h, 2.) reflux, 1.5 h 11: 71 percent / a) conc. HCl, b) Dowex 1-X8, OH(1-)-form / a) MeOH, reflux, 30 min, b) H2O View Scheme

1: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature 2: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating 3: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 4: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 5: 80 percent / pyridine / 14 h / Ambient temperature 6: 1.) H2, 2.) Et3N / 1.) Pd(OH)2 / 1.) MeOH, 1 atm, 1 h, 2.) reflux, 1.5 h 7: 71 percent / a) conc. HCl, b) Dowex 1-X8, OH(1-)-form / a) MeOH, reflux, 30 min, b) H2O View Scheme

1: 81 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 2: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature 3: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating 4: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 5: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 6: 80 percent / pyridine / 14 h / Ambient temperature 7: 1.) H2, 2.) Et3N / 1.) Pd(OH)2 / 1.) MeOH, 1 atm, 1 h, 2.) reflux, 1.5 h 8: 71 percent / a) conc. HCl, b) Dowex 1-X8, OH(1-)-form / a) MeOH, reflux, 30 min, b) H2O View Scheme

hydrogenchloride in ethanol Inert atmosphere;