1: H2, quinoline / 5percent Pd/BaSO4 / pyridine / Ambient temperature 2: 69 percent / AlI3, (+)-limonene / CS2 / 1.) r.t., 10 min, 2.) reflux, 30 min View Scheme

<b>Multi-step reaction with 8 steps<br /> </b>1: 99 percent / pyridine / 3.5 h / Ambient temperature<br />2: 73 percent / dichloromaleic anhydride / 200 &deg;C<br />3: 99 percent / 2 M KOH / ethanol / 19 h / Heating<br />4: 72 percent / CBr₄, PPh₃ / CH₂Cl₂ / 6 h / Ambient temperature<br />5: n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 3.5 h, 2.) -78 deg C to r.t., 17 h<br />6: p-TsOH*H₂O / methanol / 1 h / Heating<br />7: 68 percent / CBr₄, PPh₃ / diethyl ether; CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 17 h<br />8: 1.) EtMgBr, 2.) CuCN / 1.) THF, reflux, 1 h; r.t., 15 min, 2.) 0 deg C, 1 h; r.t., 2.75 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 3.5 h, 2.) -78 deg C to r.t., 17 h<br />2: p-TsOH*H₂O / methanol / 1 h / Heating<br />3: 68 percent / CBr₄, PPh₃ / diethyl ether; CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 17 h<br />4: 1.) EtMgBr, 2.) CuCN / 1.) THF, reflux, 1 h; r.t., 15 min, 2.) 0 deg C, 1 h; r.t., 2.75 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 72 percent / CBr₄, PPh₃ / CH₂Cl₂ / 6 h / Ambient temperature<br />2: n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 3.5 h, 2.) -78 deg C to r.t., 17 h<br />3: p-TsOH*H₂O / methanol / 1 h / Heating<br />4: 68 percent / CBr₄, PPh₃ / diethyl ether; CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 17 h<br />5: 1.) EtMgBr, 2.) CuCN / 1.) THF, reflux, 1 h; r.t., 15 min, 2.) 0 deg C, 1 h; r.t., 2.75 h<br /> <br /> &nbsp;