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.) DMSO, pyridine, CF3COOH, 2.) dicyclohexylcarbodiimide / 1.) benzene, RT, 15 min, 2.) benzene, RT, 6 h 5: 1.) potassium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 20 min, 2.) THF, 20 min 6: 81.2 percent / pyridine*(HF)x / tetrahydrofuran / 2 h / Ambient temperature 7: 69 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 0.5 h / Ambient temperature 8: 15 percent / Ce(NH4)2(NO3)6 (CAN), H2O / acetonitrile / 0.42 h / Ambient temperature View Scheme

ammonium cerium(IV) nitrate; water in acetonitrile 0.416667 h; Ambient temperature;

1: 68 percent / DEAD, PH3P / benzene 2: 68 percent / Ce(NH4)2(NO3)6 / H2O; acetonitrile 3: HOAc / tetrahydrofuran; H2O / 60 °C View Scheme

1: 98 percent / pyridine, (HF)x / tetrahydrofuran 2: 68 percent / DEAD, PH3P / benzene 3: 68 percent / Ce(NH4)2(NO3)6 / H2O; acetonitrile 4: HOAc / tetrahydrofuran; H2O / 60 °C View Scheme

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

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

1: 95 percent / 1.) nBuLi 2: -78 °C 3: LiOH 4: NaI / acetone 6: 81 percent / KN(SiMe3)2 / tetrahydrofuran / 0 °C 7: 98 percent / pyridine, (HF)x / tetrahydrofuran 8: 68 percent / DEAD, PH3P / benzene 9: 68 percent / Ce(NH4)2(NO3)6 / H2O; acetonitrile 10: HOAc / tetrahydrofuran; H2O / 60 °C View Scheme

1: LiOH 2: NaI / acetone 4: 81 percent / KN(SiMe3)2 / tetrahydrofuran / 0 °C 5: 98 percent / pyridine, (HF)x / tetrahydrofuran 6: 68 percent / DEAD, PH3P / benzene 7: 68 percent / Ce(NH4)2(NO3)6 / H2O; acetonitrile 8: HOAc / tetrahydrofuran; H2O / 60 °C View Scheme

1: NaI / acetone 3: 81 percent / KN(SiMe3)2 / tetrahydrofuran / 0 °C 4: 98 percent / pyridine, (HF)x / tetrahydrofuran 5: 68 percent / DEAD, PH3P / benzene 6: 68 percent / Ce(NH4)2(NO3)6 / H2O; acetonitrile 7: HOAc / tetrahydrofuran; H2O / 60 °C View Scheme

1: -78 °C 2: LiOH 3: NaI / acetone 5: 81 percent / KN(SiMe3)2 / tetrahydrofuran / 0 °C 6: 98 percent / pyridine, (HF)x / tetrahydrofuran 7: 68 percent / DEAD, PH3P / benzene 8: 68 percent / Ce(NH4)2(NO3)6 / H2O; acetonitrile 9: HOAc / tetrahydrofuran; H2O / 60 °C View Scheme