sulfuric acid 1.) ether, -10 deg C, 3 h, 2.) 1h; Yield given. Multistep reaction. Title compound not separated from byproducts;

quinoline; toluene-4-sulfonic acid in toluene T=130 - 140°C;

in tetrahydrofuran; water; pentane

toluene-4-sulfonic acid; sodium sulfate in benzene 1 h; Heating;

magnesium sulfate; hydroquinone in benzene T=70°C; 7.5 h;

1: 93 percent / H2 / Pd/C / methanol / 50 h / 20 °C 2: PCC / CH2Cl2 / 2 h / 20 °C 3: 82 percent / diethyl ether / 15 h / 20 °C 4: 1.) O3, O2, 2.) Me2S, 3.) Na2SO4, TsOH*H2O / 1.) CH2Cl2, MeOH, -65 deg C, 2.) -60 deg C, 1h; -15 deg C, 1 h; 0 deg C, 1 h; 20 deg C, 12 h, 3.) benzene, reflux, 1 h View Scheme

1: ZnCl2 / ethyl acetate / 24 h / 20 °C 2: H2, 2,4-dimethoxy-2-ethoxy-6,10-dimethylundeca-5,9-diene / Ni / ethanol / 50 °C / 38000 - 60800 Torr 3: pyridinium chlorochromate, methoxy alcohol (VIb) / CH2Cl2 / 5 h / 20 - 22 °C 4: 80 percent / toluene-p-sulfonic acid, quinoline / toluene / 130 - 140 °C View Scheme

1: 79 percent / H2 / Pd/C / hexane / 20 - 25 °C / 68400 Torr 2: 52 percent / aq. NaOH / 3 h / 20 °C 3: 80 percent / toluene-p-sulfonic acid, sodium sulfate / benzene / 1 h / Heating View Scheme

1: H2, 2,4-dimethoxy-2-ethoxy-6,10-dimethylundeca-5,9-diene / Ni / ethanol / 50 °C / 38000 - 60800 Torr 2: pyridinium chlorochromate, methoxy alcohol (VIb) / CH2Cl2 / 5 h / 20 - 22 °C 3: 80 percent / toluene-p-sulfonic acid, quinoline / toluene / 130 - 140 °C View Scheme

1: 87 percent / conc. perchloric acid / ethanol / 1 h 2: ZnCl2 / ethyl acetate / 24 h / 20 °C 3: H2, 2,4-dimethoxy-2-ethoxy-6,10-dimethylundeca-5,9-diene / Ni / ethanol / 50 °C / 38000 - 60800 Torr 4: pyridinium chlorochromate, methoxy alcohol (VIb) / CH2Cl2 / 5 h / 20 - 22 °C 5: 80 percent / toluene-p-sulfonic acid, quinoline / toluene / 130 - 140 °C View Scheme