dicyclohexyl-carbodiimide in dichloromethane 2 h;

1: 1.) Tl(CO2CF3)3, TFA; 2.) MgO, LiCl; 3.) 1N NaOH / 2.) PdCl2 / 1.) 75 deg C, 24 h; 2.) r.t., 24 h; 3.) MeOH, r.t., 2 h 2: 95 percent / DCC / CH2Cl2 / 2 h View Scheme

1: 97 percent / imidazole 2: 1) n-BuLi / 1) hexane, ether, -30 to 0 deg C in 2 h, 2) ether, -50 deg C, 3 h 3: 93 percent / NH3OHCl, NaOH / ethanol / 16 h / Heating 4: 70 percent / pyridine / 3 h / Heating 5: 86 percent / liq. NH3 / diethyl ether / 12 h / Ambient temperature 6: 91 percent / Ag2O / diethyl ether / 1 h 7: 92 percent / conc. HCl / methanol 8: 72 percent / 0.2N KOH, KMnO4 / dioxane / 2 h / Ambient temperature 9: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature View Scheme

1: 89 percent / NH3OHCl, NaOH / ethanol / 16 h / Heating 2: 92 percent / pyridine / 3 h / Heating 3: 91 percent / liq. NH3 / diethyl ether / 12 h / Ambient temperature 4: 91 percent / Ag2O / diethyl ether / 1 h 5: 58 percent / KMnO4 / pyridine; H2O / 20 h / 50 °C 6: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature View Scheme

1: 58 percent / KMnO4 / pyridine; H2O / 20 h / 50 °C 2: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature View Scheme

1: 91 percent / Ag2O / diethyl ether / 1 h 2: 58 percent / KMnO4 / pyridine; H2O / 20 h / 50 °C 3: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature View Scheme

1: 1) n-BuLi / 1) hexane, ether, -30 to 0 deg C in 2 h, 2) ether, -50 deg C, 3 h 2: 57 percent / NH3OHCl, NaOH / ethanol / 16 h / Heating 3: 87 percent / pyridine / 3 h / Heating 4: 80 percent / NH3 / diethyl ether / 12 h / Ambient temperature 5: 92 percent / Ag2O / diethyl ether / 1 h 6: 86 percent / TFA / CH2Cl2 / 2 h / Ambient temperature 7: 72 percent / 0.2N KOH, KMnO4 / dioxane / 2 h / Ambient temperature 8: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature View Scheme

1: 1) n-BuLi / 1) hexane, ether, -30 to 0 deg C in 2 h, 2) ether, -50 deg C, 3 h 2: 93 percent / NH3OHCl, NaOH / ethanol / 16 h / Heating 3: 70 percent / pyridine / 3 h / Heating 4: 86 percent / liq. NH3 / diethyl ether / 12 h / Ambient temperature 5: 91 percent / Ag2O / diethyl ether / 1 h 6: 92 percent / conc. HCl / methanol 7: 72 percent / 0.2N KOH, KMnO4 / dioxane / 2 h / Ambient temperature 8: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature View Scheme

1: 57 percent / NH3OHCl, NaOH / ethanol / 16 h / Heating 2: 87 percent / pyridine / 3 h / Heating 3: 80 percent / NH3 / diethyl ether / 12 h / Ambient temperature 4: 92 percent / Ag2O / diethyl ether / 1 h 5: 86 percent / TFA / CH2Cl2 / 2 h / Ambient temperature 6: 72 percent / 0.2N KOH, KMnO4 / dioxane / 2 h / Ambient temperature 7: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature View Scheme

1: 86 percent / TFA / CH2Cl2 / 2 h / Ambient temperature 2: 72 percent / 0.2N KOH, KMnO4 / dioxane / 2 h / Ambient temperature 3: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature View Scheme