1.1: O3 / CH2Cl2 / -78 °C 1.2: Me2S / CH2Cl2 2.1: K10 montmorillonite 3.1: 87 percent / 4-(dimethylamino)pyridinium bromide perbromide; 4-(dimethylamino)pyridine / CH2Cl2 4.1: 90 percent / LiHMDS / tetrahydrofuran 5.1: BuLi; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran 6.1: hydrochloric acid / tetrahydrofuran 7.1: diethyl ether / -100 °C 8.1: imidazole / dimethylformamide 9.1: O3; Sudan red 7B / methanol 9.2: 94 percent / Me2S / methanol 10.1: 73 percent / TiCl4; diisopropylethylamine / CH2Cl2 / -78 °C 11.1: hydrochloric acid / tetrahydrofuran 12.1: (+)-10-camphorsulfonic acid 13.1: pyridine / CH2Cl2 / -10 °C 14.1: 15[crown]-5 / tetrahydrofuran 15.1: 70 percent / [Mo{N(tBu)(3,5-Me2C6H3)}3] / toluene; CH2Cl2 / 80 °C 16.1: 100 percent / H2 / Lindlar catalyst / CH2Cl2 17.1: 78 percent / ceric ammonium nitrate / acetonitrile; H2O View Scheme

1.1: K10 montmorillonite 2.1: 87 percent / 4-(dimethylamino)pyridinium bromide perbromide; 4-(dimethylamino)pyridine / CH2Cl2 3.1: 90 percent / LiHMDS / tetrahydrofuran 4.1: BuLi; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran 5.1: hydrochloric acid / tetrahydrofuran 6.1: diethyl ether / -100 °C 7.1: imidazole / dimethylformamide 8.1: O3; Sudan red 7B / methanol 8.2: 94 percent / Me2S / methanol 9.1: 73 percent / TiCl4; diisopropylethylamine / CH2Cl2 / -78 °C 10.1: hydrochloric acid / tetrahydrofuran 11.1: (+)-10-camphorsulfonic acid 12.1: pyridine / CH2Cl2 / -10 °C 13.1: 15[crown]-5 / tetrahydrofuran 14.1: 70 percent / [Mo{N(tBu)(3,5-Me2C6H3)}3] / toluene; CH2Cl2 / 80 °C 15.1: 100 percent / H2 / Lindlar catalyst / CH2Cl2 16.1: 78 percent / ceric ammonium nitrate / acetonitrile; H2O View Scheme

1.1: diethyl ether / -100 °C 2.1: imidazole / dimethylformamide 3.1: O3; Sudan red 7B / methanol 3.2: 94 percent / Me2S / methanol 4.1: 73 percent / TiCl4; diisopropylethylamine / CH2Cl2 / -78 °C 5.1: hydrochloric acid / tetrahydrofuran 6.1: (+)-10-camphorsulfonic acid 7.1: pyridine / CH2Cl2 / -10 °C 8.1: 15[crown]-5 / tetrahydrofuran 9.1: 70 percent / [Mo{N(tBu)(3,5-Me2C6H3)}3] / toluene; CH2Cl2 / 80 °C 10.1: 100 percent / H2 / Lindlar catalyst / CH2Cl2 11.1: 78 percent / ceric ammonium nitrate / acetonitrile; H2O View Scheme

1.1: 87 percent / 4-(dimethylamino)pyridinium bromide perbromide; 4-(dimethylamino)pyridine / CH2Cl2 2.1: 90 percent / LiHMDS / tetrahydrofuran 3.1: BuLi; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran 4.1: hydrochloric acid / tetrahydrofuran 5.1: diethyl ether / -100 °C 6.1: imidazole / dimethylformamide 7.1: O3; Sudan red 7B / methanol 7.2: 94 percent / Me2S / methanol 8.1: 73 percent / TiCl4; diisopropylethylamine / CH2Cl2 / -78 °C 9.1: hydrochloric acid / tetrahydrofuran 10.1: (+)-10-camphorsulfonic acid 11.1: pyridine / CH2Cl2 / -10 °C 12.1: 15[crown]-5 / tetrahydrofuran 13.1: 70 percent / [Mo{N(tBu)(3,5-Me2C6H3)}3] / toluene; CH2Cl2 / 80 °C 14.1: 100 percent / H2 / Lindlar catalyst / CH2Cl2 15.1: 78 percent / ceric ammonium nitrate / acetonitrile; H2O View Scheme

1.1: hydrochloric acid / tetrahydrofuran 2.1: diethyl ether / -100 °C 3.1: imidazole / dimethylformamide 4.1: O3; Sudan red 7B / methanol 4.2: 94 percent / Me2S / methanol 5.1: 73 percent / TiCl4; diisopropylethylamine / CH2Cl2 / -78 °C 6.1: hydrochloric acid / tetrahydrofuran 7.1: (+)-10-camphorsulfonic acid 8.1: pyridine / CH2Cl2 / -10 °C 9.1: 15[crown]-5 / tetrahydrofuran 10.1: 70 percent / [Mo{N(tBu)(3,5-Me2C6H3)}3] / toluene; CH2Cl2 / 80 °C 11.1: 100 percent / H2 / Lindlar catalyst / CH2Cl2 12.1: 78 percent / ceric ammonium nitrate / acetonitrile; H2O View Scheme

1.1: BuLi; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran 2.1: hydrochloric acid / tetrahydrofuran 3.1: diethyl ether / -100 °C 4.1: imidazole / dimethylformamide 5.1: O3; Sudan red 7B / methanol 5.2: 94 percent / Me2S / methanol 6.1: 73 percent / TiCl4; diisopropylethylamine / CH2Cl2 / -78 °C 7.1: hydrochloric acid / tetrahydrofuran 8.1: (+)-10-camphorsulfonic acid 9.1: pyridine / CH2Cl2 / -10 °C 10.1: 15[crown]-5 / tetrahydrofuran 11.1: 70 percent / [Mo{N(tBu)(3,5-Me2C6H3)}3] / toluene; CH2Cl2 / 80 °C 12.1: 100 percent / H2 / Lindlar catalyst / CH2Cl2 13.1: 78 percent / ceric ammonium nitrate / acetonitrile; H2O View Scheme

1.1: 90 percent / LiHMDS / tetrahydrofuran 2.1: BuLi; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran 3.1: hydrochloric acid / tetrahydrofuran 4.1: diethyl ether / -100 °C 5.1: imidazole / dimethylformamide 6.1: O3; Sudan red 7B / methanol 6.2: 94 percent / Me2S / methanol 7.1: 73 percent / TiCl4; diisopropylethylamine / CH2Cl2 / -78 °C 8.1: hydrochloric acid / tetrahydrofuran 9.1: (+)-10-camphorsulfonic acid 10.1: pyridine / CH2Cl2 / -10 °C 11.1: 15[crown]-5 / tetrahydrofuran 12.1: 70 percent / [Mo{N(tBu)(3,5-Me2C6H3)}3] / toluene; CH2Cl2 / 80 °C 13.1: 100 percent / H2 / Lindlar catalyst / CH2Cl2 14.1: 78 percent / ceric ammonium nitrate / acetonitrile; H2O 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.) DMSO, pyridine, CF3COOH, 2.) dicyclohexylcarbodiimide / 1.) benzene, RT, 15 min, 2.) benzene, RT, 6 h 4: 1.) potassium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 20 min, 2.) THF, 20 min 5: 81.2 percent / pyridine*(HF)x / tetrahydrofuran / 2 h / Ambient temperature 6: 69 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 0.5 h / Ambient temperature 7: 15 percent / Ce(NH4)2(NO3)6 (CAN), H2O / acetonitrile / 0.42 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

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.) DMSO, pyridine, CF3COOH, 2.) dicyclohexylcarbodiimide / 1.) benzene, RT, 15 min, 2.) benzene, RT, 6 h 6: 1.) potassium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 20 min, 2.) THF, 20 min 7: 81.2 percent / pyridine*(HF)x / tetrahydrofuran / 2 h / Ambient temperature 8: 69 percent / PPh3, diethyl azodicarboxylate (DEAD) / benzene / 0.5 h / Ambient temperature 9: 15 percent / Ce(NH4)2(NO3)6 (CAN), H2O / acetonitrile / 0.42 h / Ambient temperature View Scheme