1: H2 / Lindlar catalyst 2: pyridine / CH2Cl2 / 0 °C 3: Et3N / -20 °C 4: 1.) NaOMe, MeOH, 2.) Collins reagent, 3.) DBU View Scheme

1: 100 percent / quinoline, H2 / Lindlar / methanol / 760 Torr 2: 84 percent / pyridine / CH2Cl2 / 1 h / 0 °C 3: 27 g / Et3N / 0.33 h / -20 °C 4: 1.) NaOMe / 1.) MeOH, 0 deg C, 30 min, 1.5 h, r.t., 2.) ether 5: 20 g / CrO3, Celite / CH2Cl2; pyridine / 0.17 h / 0 °C 6: DBU / toluene / 0.33 h 7: diethyl ether / 1 h / -78 °C 8: CrO3, Celite / CH2Cl2; pyridine / 0.17 h / 0 °C View Scheme