1: 99 percent / DMSO, (COCl)2, Et3N / CH2Cl2 2: 96 percent / PPh3 / benzene / 80 °C 3: 84 percent / n-BuLi / tetrahydrofuran / -78 °C 4: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation 5: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C 6: 88 percent / H2 / Lindlar / methanol 7: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 8: (C6H11)2NMgBr / methanol / -55 °C 9: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: DMSO, (COCl)2, Et3N 2: NaH / dimethylformamide; tetrahydrofuran / 0 °C 3: H2 / Pd-C / ethyl acetate / Ambient temperature 4: tetrahydrofuran / -78 °C 5: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, -78 deg C 6: Et3N / 0 °C 7: 1N-HCl / tetrahydrofuran / Ambient temperature 8: K2CO3 / methanol 9: NaH / tetrahydrofuran / Ambient temperature 10: camphorsulfonic acid / CH2Cl2 / 0 °C 11: DMSO, (COCl)2, Et3N / CH2Cl2 12: 28 percent / (Ph3P)3RhCl / acetonitrile / 160 °C 13: DDQ / CH2Cl2; H2O 14: DMSO, (COCl)2 / CH2Cl2 15: TsOH / benzene 16: H2 / Pd-C / ethyl acetate 17: CrO3, H2SO4 / acetone 18: 2N-HCl / tetrahydrofuran / Ambient temperature 19: (C6H11)2NMgBr / methanol / -55 °C 20: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: LiAlH4 / diethyl ether / 0 °C 2: camphorsulfonic acid / Ambient temperature 3: H2 / Pd-C / ethanol / Ambient temperature 4: DMSO, (COCl)2, Et3N 5: NaH / dimethylformamide; tetrahydrofuran / 0 °C 6: H2 / Pd-C / ethyl acetate / Ambient temperature 7: tetrahydrofuran / -78 °C 8: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, -78 deg C 9: Et3N / 0 °C 10: 1N-HCl / tetrahydrofuran / Ambient temperature 11: K2CO3 / methanol 12: NaH / tetrahydrofuran / Ambient temperature 13: camphorsulfonic acid / CH2Cl2 / 0 °C 14: DMSO, (COCl)2, Et3N / CH2Cl2 15: 28 percent / (Ph3P)3RhCl / acetonitrile / 160 °C 16: DDQ / CH2Cl2; H2O 17: DMSO, (COCl)2 / CH2Cl2 18: TsOH / benzene 19: H2 / Pd-C / ethyl acetate 20: CrO3, H2SO4 / acetone 21: 2N-HCl / tetrahydrofuran / Ambient temperature 22: (C6H11)2NMgBr / methanol / -55 °C 23: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, -78 deg C 2: Et3N / 0 °C 3: 1N-HCl / tetrahydrofuran / Ambient temperature 4: K2CO3 / methanol 5: NaH / tetrahydrofuran / Ambient temperature 6: camphorsulfonic acid / CH2Cl2 / 0 °C 7: DMSO, (COCl)2, Et3N / CH2Cl2 8: 28 percent / (Ph3P)3RhCl / acetonitrile / 160 °C 9: DDQ / CH2Cl2; H2O 10: DMSO, (COCl)2 / CH2Cl2 11: TsOH / benzene 12: H2 / Pd-C / ethyl acetate 13: CrO3, H2SO4 / acetone 14: 2N-HCl / tetrahydrofuran / Ambient temperature 15: (C6H11)2NMgBr / methanol / -55 °C 16: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

2: 99 percent / DMSO, (COCl)2, Et3N / CH2Cl2 3: 96 percent / PPh3 / benzene / 80 °C 4: 84 percent / n-BuLi / tetrahydrofuran / -78 °C 5: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation 6: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C 7: 88 percent / H2 / Lindlar / methanol 8: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 9: (C6H11)2NMgBr / methanol / -55 °C 10: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

3 A molecular sieve; trifluoroacetic acid in dichloromethane 0.333333 h; Ambient temperature;

1: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation 2: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C 3: 88 percent / H2 / Lindlar / methanol 4: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 5: (C6H11)2NMgBr / methanol / -55 °C 6: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: 96 percent / PPh3 / benzene / 80 °C 2: 84 percent / n-BuLi / tetrahydrofuran / -78 °C 3: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation 4: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C 5: 88 percent / H2 / Lindlar / methanol 6: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 7: (C6H11)2NMgBr / methanol / -55 °C 8: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: 84 percent / n-BuLi / tetrahydrofuran / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation 3: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C 4: 88 percent / H2 / Lindlar / methanol 5: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 6: (C6H11)2NMgBr / methanol / -55 °C 7: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: 88 percent / H2 / Lindlar / methanol 2: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 3: (C6H11)2NMgBr / methanol / -55 °C 4: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme