1: toluene / Irradiation 2: 1.) OsO4, NaIO4, 2.) NaBH4 / 1.) THF,H2O, 2.) ethanol 3: pyridine 4: dimethylformamide 5: CH3CO3H, NaHCO3 / CH2Cl2 6: 1.) LDA / 1.) THF, 0 deg C, 15 min 7: pyridine / 23 °C 8: Li, NH3 / tetrahydrofuran / -78 °C 9: 2.) K2CO3 / 1.) 1,2-dichloroethane, 70 deg C, 24 h, 2.) MeOH, 0 deg C 10: 1.) LiN(SiMe3)2 / 1.) dioxane 11: 80percent HOAc 12: Na2CO3, KOH / ethanol; tetrahydrofuran View Scheme