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: 96.7 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C 2: 1.) DMSO, pyridine, CF3COOH, 2.) dicyclohexylcarbodiimide / 1.) benzene, RT, 15 min, 2.) benzene, RT, 6 h 3: 1.) potassium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 20 min, 2.) THF, 20 min 4: 81.2 percent / pyridine*(HF)x / tetrahydrofuran / 2 h / Ambient temperature 5: 69 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 0.5 h / Ambient temperature 6: 15 percent / Ce(NH4)2(NO3)6 (CAN), H2O / acetonitrile / 0.42 h / Ambient temperature View Scheme