1: H2, quinoline / 5percent Pd/BaSO4 / pyridine / 1.92 h / 750.06 Torr / Ambient temperature 2: 63 percent / AlI3, (+)-limonene / CS2 / 1.) r.t., 10 min, 2.) reflux, 30 min View Scheme

1: p-TsOH*H2O / methanol / 1 h / Heating 2: 68 percent / CBr4, PPh3 / diethyl ether; CH2Cl2 / 1.) 0 deg C, 1 h, 2.) r.t., 17 h 3: 1.) EtMgBr, 2.) CuCN / 1.) THF, reflux, 1 h; r.t., 15 min, 2.) 0 deg C, 30 min; r.t., 15 h 4: H2, quinoline / 5percent Pd/BaSO4 / pyridine / 1.92 h / 750.06 Torr / Ambient temperature 5: 63 percent / AlI3, (+)-limonene / CS2 / 1.) r.t., 10 min, 2.) reflux, 30 min View Scheme