1: Hg(OAc)2 / 24 h / Heating 2: xylene / 3 h / 140 °C 3: 62 percent / tetrahydrofuran / 2 h / Heating 4: 79 percent / t-BuOOH, V2O5 5: n-BuLi / tetrahydrofuran / 1 h / -78 °C 6: PdCl2, CuCl, O2 / dimethylformamide; H2O / 12 h / Ambient temperature 7: 1.) DBU, CH2Cl2, reflux, 1 hr 2.) Pd/C, H2, EtOH View Scheme

1: Hg(OAc)2 / 24 h / Heating 2: xylene / 3 h / 140 °C 3: 62 percent / tetrahydrofuran / 2 h / Heating 4: 79 percent / t-BuOOH, V2O5 5: n-BuLi / tetrahydrofuran / 1 h / -78 °C 6: PdCl2, CuCl, O2 / dimethylformamide; H2O / 12 h / Ambient temperature 7: 1.) DBU, CH2Cl2, reflux, 1 hr 2.) Pd/C, H2, EtOH View Scheme

1: Hg(OAc)2 / 24 h / Heating 2: xylene / 3 h / 140 °C 3: 81 percent / tetrahydrofuran / 2 h / Heating 4: NaIO4 / H2O; acetone 5: 1.) Ac2O, (CF3CO)2O, r.t., 48 hr 2.) EtOH, 1N NaOH, r.t., 0.5 hr View Scheme

1: Hg(OAc)2 / 24 h / Heating 2: xylene / 3 h / 140 °C 3: 81 percent / tetrahydrofuran / 2 h / Heating 4: NaIO4 / H2O; acetone 5: Heating; distillative thermolysis View Scheme

1: 83 percent / Hg(OAc)2 / 12 h / Heating 2: 81 percent / xylene / 3 h / Heating 3: 80 percent / diethyl ether / 0 °C 4: 98 percent / pyridine / 12 h / Ambient temperature 6: 82 percent / LiAlH4 / tetrahydrofuran / 0 °C 7: 94 percent / N-Chlorosuccinimide, dimethyl sulfide / 1.) toluene, -23 deg C, 2h; 2.) toluene, triethylamine, -23 deg C, 10 min. 8: 94 percent / n-BuLi / tetrahydrofuran / 1 h / Heating 9: 89 percent / 30percent H2O2 / methanol / 12 h / Ambient temperature 10: 90 percent / NaHCO3 / toluene / 2 h / Heating View Scheme

diisobutylaluminium hydride

lithium aluminium tetrahydride in diethyl ether

1: 1.) Zn, 2.) CuCN, LiCl 2: DIBAL / tetrahydrofuran / 5 h / -78 - 20 °C View Scheme

titanium tetrachloride

1: 82 percent / K2CO3, KI / acetone 2: 90 percent / NaH, paraformaldehyde / tetrahydrofuran / 4 h / Heating 3: 85 percent / DIBAL View Scheme