1: pyridinium chlorochromate; NaOAc; molecular sieves / CH2Cl2 / 1 h / Ambient temperature 2: 1.) n-BuLi in n-hexane/diisopropylamine / 1.) THF, -74 deg C, 80 min,2.) -70 deg C, 30 min 3: 84 percent / (i-Pr)2NEt / CH2Cl2 / 89 h / Ambient temperature 4: 82 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 5: 84 percent / quinoline; H2 / 5percent Pd/BaSO4 / methanol / Ambient temperature 6: LiOH*H2O / H2O; tetrahydrofuran / 5 h / Ambient temperature 7: 1.) 2,4,6-trichlorobenzoyl chloride, NEt3,2.) 4-(dimethylamino)pyridine / 1.) THF, room temp., 8.5 h, 2.) toluene, reflux, 11.5 h 8: TiCl4 / CH2Cl2 / 0.02 h / 0 °C 9: 5.7 mg / pyridinium dichromate / CH2Cl2 / 24 h / Ambient temperature View Scheme

Multi-step reaction with 7 steps 1: 1) pyridine / 1) 0 deg C, 2) heating2: 60 percent / thionyl chloride / 1 h / Heating3: 100 percent / diethyl ether4: 90 percent / silver oxide / dioxane / 1 h / Heating5: 91 percent / NaOMe, MeOH / 15 h6: 90 percent / toluene-p-sulphonic acid / diethyl ether / 5 h / 10 °C7: 96 percent / LAH / diethyl ether / 8 h / 0 °C