1: 95 percent / p-toluenesulfonic acid monohydrate / 0.33 h / Heating 2: 25 g / triethylamine / tetrahydrofuran / 0.5 h / Ambient temperature 3: 0.5 M H2SO4 / acetone / 0.08 h / Heating View Scheme

1: p-toluenesulfonic acid / acetone / 23 °C 2: 1.) MeLi / 1.) THF, -78 deg C 3: toluene / Irradiation 4: 1.) OsO4, NaIO4, 2.) NaBH4 / 1.) THF,H2O, 2.) ethanol 5: pyridine 6: dimethylformamide 7: CH3CO3H, NaHCO3 / CH2Cl2 8: 1.) LDA / 1.) THF, 0 deg C, 15 min 9: pyridine / 23 °C 10: Li, NH3 / tetrahydrofuran / -78 °C 11: 2.) K2CO3 / 1.) 1,2-dichloroethane, 70 deg C, 24 h, 2.) MeOH, 0 deg C 12: 1.) LiN(SiMe3)2 / 1.) dioxane 13: 80percent HOAc 14: Na2CO3, KOH / ethanol; tetrahydrofuran View Scheme

pyridine