1: 94 percent / methanol; tetrahydrofuran / -78 °C 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

 in  tetrahydrofuran; methanol T=-78°C;   

Multi-step reaction with 3 steps 1: 94 percent / methanol; tetrahydrofuran / -78 °C2: 57 percent / lithium diisopropylamine / tetrahydrofuran; hexamethylphosphoric acid triamide / -55 °C3: 87 percent / LiAlH4 / tetrahydrofuran / -78 - 20 °C  

Multi-step reaction with 4 steps 1: 94 percent / methanol; tetrahydrofuran / -78 °C2: 57 percent / lithium diisopropylamine / tetrahydrofuran; hexamethylphosphoric acid triamide / -55 °C3: 87 percent / LiAlH4 / tetrahydrofuran / -78 - 20 °C4: imidazole, pyridinum toluene-p-sulphonate / 1.) dimethylformamide 2.) Ch2Cl2