1: 71 percent / n-Bu4NF / dimethylsulfoxide; tetrahydrofuran / 0.5 h / Ambient temperature 2: 1) Ph3P, diethyl azodicarboxylate (DEAD) / 1) benzene, r.t., 5 min, 2) benzene, r.t., 2 h 3: 72 percent / aq. AcOH / 2 h / 60 °C View Scheme

1: 76.8 percent / Al2O3, pyridinium chlorochromate (PCC) / CH2Cl2 / 0.5 h / Ambient temperature 2: 78.4 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 - 20 °C 3: 1.) sodium bis(trimethylsilyl)amide, hexamethylphosphoric triamide (HMPA) / 1.) THF, -78 deg C, 30 min, 2.) THF, 30 min 4: 89.3 percent / pyridine*(HF)x / tetrahydrofuran / 1 h / 0 °C 5: 28 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 48 h / Ambient temperature 6: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.05 h / Ambient temperature 7: 49 percent / 3 N aq. HCl / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 78.4 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 - 20 °C 2: 1.) sodium bis(trimethylsilyl)amide, hexamethylphosphoric triamide (HMPA) / 1.) THF, -78 deg C, 30 min, 2.) THF, 30 min 3: 89.3 percent / pyridine*(HF)x / tetrahydrofuran / 1 h / 0 °C 4: 28 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 48 h / Ambient temperature 5: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.05 h / Ambient temperature 6: 49 percent / 3 N aq. HCl / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 1.) sodium bis(trimethylsilyl)amide, hexamethylphosphoric triamide (HMPA) / 1.) THF, -78 deg C, 30 min, 2.) THF, 30 min 2: 89.3 percent / pyridine*(HF)x / tetrahydrofuran / 1 h / 0 °C 3: 28 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 48 h / Ambient temperature 4: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.05 h / Ambient temperature 5: 49 percent / 3 N aq. HCl / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 28 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 48 h / Ambient temperature 2: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.05 h / Ambient temperature 3: 49 percent / 3 N aq. HCl / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 89.3 percent / pyridine*(HF)x / tetrahydrofuran / 1 h / 0 °C 2: 28 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 48 h / Ambient temperature 3: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.05 h / Ambient temperature 4: 49 percent / 3 N aq. HCl / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 93 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature 2: 96.7 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C 3: 1.) tert-butyllithium, 2.) O2 / 1.) THF, pentane, -78 deg C, 5 min 4: 76.8 percent / Al2O3, pyridinium chlorochromate (PCC) / CH2Cl2 / 0.5 h / Ambient temperature 5: 78.4 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 - 20 °C 6: 1.) sodium bis(trimethylsilyl)amide, hexamethylphosphoric triamide (HMPA) / 1.) THF, -78 deg C, 30 min, 2.) THF, 30 min 7: 89.3 percent / pyridine*(HF)x / tetrahydrofuran / 1 h / 0 °C 8: 28 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 48 h / Ambient temperature 9: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.05 h / Ambient temperature 10: 49 percent / 3 N aq. HCl / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 96.7 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C 2: 1.) tert-butyllithium, 2.) O2 / 1.) THF, pentane, -78 deg C, 5 min 3: 76.8 percent / Al2O3, pyridinium chlorochromate (PCC) / CH2Cl2 / 0.5 h / Ambient temperature 4: 78.4 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 - 20 °C 5: 1.) sodium bis(trimethylsilyl)amide, hexamethylphosphoric triamide (HMPA) / 1.) THF, -78 deg C, 30 min, 2.) THF, 30 min 6: 89.3 percent / pyridine*(HF)x / tetrahydrofuran / 1 h / 0 °C 7: 28 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 48 h / Ambient temperature 8: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.05 h / Ambient temperature 9: 49 percent / 3 N aq. HCl / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 72.5 percent / 2 N aq. HCl / tetrahydrofuran / 24 h / Ambient temperature 2: 74.6 percent / camphorsulfonic acid / toluene / 4.5 h / Ambient temperature 3: 93 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature 4: 96.7 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C 5: 1.) tert-butyllithium, 2.) O2 / 1.) THF, pentane, -78 deg C, 5 min 6: 76.8 percent / Al2O3, pyridinium chlorochromate (PCC) / CH2Cl2 / 0.5 h / Ambient temperature 7: 78.4 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 - 20 °C 8: 1.) sodium bis(trimethylsilyl)amide, hexamethylphosphoric triamide (HMPA) / 1.) THF, -78 deg C, 30 min, 2.) THF, 30 min 9: 89.3 percent / pyridine*(HF)x / tetrahydrofuran / 1 h / 0 °C 10: 28 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 48 h / Ambient temperature 11: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.05 h / Ambient temperature 12: 49 percent / 3 N aq. HCl / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 74.6 percent / camphorsulfonic acid / toluene / 4.5 h / Ambient temperature 2: 93 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature 3: 96.7 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C 4: 1.) tert-butyllithium, 2.) O2 / 1.) THF, pentane, -78 deg C, 5 min 5: 76.8 percent / Al2O3, pyridinium chlorochromate (PCC) / CH2Cl2 / 0.5 h / Ambient temperature 6: 78.4 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 - 20 °C 7: 1.) sodium bis(trimethylsilyl)amide, hexamethylphosphoric triamide (HMPA) / 1.) THF, -78 deg C, 30 min, 2.) THF, 30 min 8: 89.3 percent / pyridine*(HF)x / tetrahydrofuran / 1 h / 0 °C 9: 28 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 48 h / Ambient temperature 10: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.05 h / Ambient temperature 11: 49 percent / 3 N aq. HCl / tetrahydrofuran / 18 h / Ambient temperature View Scheme