1: (COCl)2, DMSO, Et3N / CH2Cl2 / -78 °C 2: 73 percent / KHMDS / tetrahydrofuran; toluene 3: 88 percent / DDQ / CH2Cl2; H2O 4: 88 percent / i-Pr2NEt / CH2Cl2 / 0 °C 5: 76 percent / p-toluenesulfonic acid / dimethylsulfoxide / 120 °C 6: 1.) OsO4, NMO; 2.) NaIO4 / 1.) t-BuOH, THF, H2O; 2.) THF, H2O 7: LiAlH4 / tetrahydrofuran / 0 °C 8: 87 percent / TFA / methanol 9: 89 percent / H2 / Pd/C / ethanol View Scheme