N,N,N',N',N'',N''-hexamethylphosphoric triamide; sodium hydride in N,N,N',N',N'',N''-hexamethylphosphoric triamide; water; dimethyl sulfoxide T=175°C;

1: imidazole, pyridinum toluene-p-sulphonate / 1.) dimethylformamide 2.) Ch2Cl2 2: 84 percent / NaIO4, KMnO4, Na2CO3, CH2N2 / dioxane; H2O; diethyl ether 3: 81 percent / NaH, hexamethylphosphoramide / dimethylsulfoxide; hexamethylphosphoric acid triamide; H2O / 175 °C View Scheme

1: 87 percent / LiAlH4 / tetrahydrofuran / -78 - 20 °C 2: imidazole, pyridinum toluene-p-sulphonate / 1.) dimethylformamide 2.) Ch2Cl2 3: 84 percent / NaIO4, KMnO4, Na2CO3, CH2N2 / dioxane; H2O; diethyl ether 4: 81 percent / NaH, hexamethylphosphoramide / dimethylsulfoxide; hexamethylphosphoric acid triamide; H2O / 175 °C View Scheme

1: imidazole, pyridinum toluene-p-sulphonate / 1.) dimethylformamide 2.) Ch2Cl2 2: 84 percent / NaIO4, KMnO4, Na2CO3, CH2N2 / dioxane; H2O; diethyl ether 3: 81 percent / NaH, hexamethylphosphoramide / dimethylsulfoxide; hexamethylphosphoric acid triamide; H2O / 175 °C View Scheme

1: dicyclohexylcarbodiimide, hydroxybenzotriazole / 1.) THF 2.) Et3N 2: 57 percent / lithium diisopropylamine / tetrahydrofuran; hexamethylphosphoric acid triamide / -55 °C 3: 87 percent / LiAlH4 / tetrahydrofuran / -78 - 20 °C 4: imidazole, pyridinum toluene-p-sulphonate / 1.) dimethylformamide 2.) Ch2Cl2 5: 84 percent / NaIO4, KMnO4, Na2CO3, CH2N2 / dioxane; H2O; diethyl ether 6: 81 percent / NaH, hexamethylphosphoramide / dimethylsulfoxide; hexamethylphosphoric acid triamide; H2O / 175 °C View Scheme

1: 57 percent / lithium diisopropylamine / tetrahydrofuran; hexamethylphosphoric acid triamide / -55 °C 2: 87 percent / LiAlH4 / tetrahydrofuran / -78 - 20 °C 3: imidazole, pyridinum toluene-p-sulphonate / 1.) dimethylformamide 2.) Ch2Cl2 4: 84 percent / NaIO4, KMnO4, Na2CO3, CH2N2 / dioxane; H2O; diethyl ether 5: 81 percent / NaH, hexamethylphosphoramide / dimethylsulfoxide; hexamethylphosphoric acid triamide; H2O / 175 °C View Scheme

1: imidazole, pyridinum toluene-p-sulphonate / 1.) dimethylformamide 2.) Ch2Cl2 2: 84 percent / NaIO4, KMnO4, Na2CO3, CH2N2 / dioxane; H2O; diethyl ether 3: 81 percent / NaH, hexamethylphosphoramide / dimethylsulfoxide; hexamethylphosphoric acid triamide; H2O / 175 °C View Scheme

1: 94 percent / methanol; tetrahydrofuran / -60 - 10 °C 2: dicyclohexylcarbodiimide, hydroxybenzotriazole / 1.) THF 2.) Et3N 3: 57 percent / lithium diisopropylamine / tetrahydrofuran; hexamethylphosphoric acid triamide / -55 °C 4: 87 percent / LiAlH4 / tetrahydrofuran / -78 - 20 °C 5: imidazole, pyridinum toluene-p-sulphonate / 1.) dimethylformamide 2.) Ch2Cl2 6: 84 percent / NaIO4, KMnO4, Na2CO3, CH2N2 / dioxane; H2O; diethyl ether 7: 81 percent / NaH, hexamethylphosphoramide / dimethylsulfoxide; hexamethylphosphoric acid triamide; H2O / 175 °C View Scheme

1: 84 percent / NaIO4, KMnO4, Na2CO3, CH2N2 / dioxane; H2O; diethyl ether 2: 81 percent / NaH, hexamethylphosphoramide / dimethylsulfoxide; hexamethylphosphoric acid triamide; H2O / 175 °C View Scheme

1: 72 percent / HCl / dioxane / 60 °C 2: 94 percent / methanol; tetrahydrofuran / -60 - 10 °C 3: dicyclohexylcarbodiimide, hydroxybenzotriazole / 1.) THF 2.) Et3N 4: 57 percent / lithium diisopropylamine / tetrahydrofuran; hexamethylphosphoric acid triamide / -55 °C 5: 87 percent / LiAlH4 / tetrahydrofuran / -78 - 20 °C 6: imidazole, pyridinum toluene-p-sulphonate / 1.) dimethylformamide 2.) Ch2Cl2 7: 84 percent / NaIO4, KMnO4, Na2CO3, CH2N2 / dioxane; H2O; diethyl ether 8: 81 percent / NaH, hexamethylphosphoramide / dimethylsulfoxide; hexamethylphosphoric acid triamide; H2O / 175 °C View Scheme