1: 75 percent / Et3N, DMAP / 96 h / 35 - 40 °C 2: 60 percent / pyridine, Cu(OAc), Pb(OAc)4 / benzene / 80 °C 3: 92 percent / Li, ethylene diamine / benzene / 2.5 h / Ambient temperature 4: 1) O3, 2) Zn / 1) CH2Cl2, -78 deg C, 5 min, 2) AcOH, a) -78 deg C, 5 min, b) rt, 30 min View Scheme

1: 47 percent / N,N-dimethylaniline 2: iodobenzene diacetate; I2 / CCl4 / 1.5 h / Heating; irradiation 3: 78 percent / t-BuOK / dimethylsulfoxide / 20 °C 4: O3 / methanol; CH2Cl2 / -78 °C 5: 0.17 g / NaBH4 / methanol; CH2Cl2 / -78 °C 6: 87 percent / p-toluenesulfonic acid / nitromethane / 3 h / 20 °C View Scheme

1: 75 percent / Et3N, DMAP / 96 h / 35 - 40 °C 2: 60 percent / pyridine, Cu(OAc), Pb(OAc)4 / benzene / 80 °C 3: 92 percent / Li, ethylene diamine / benzene / 2.5 h / Ambient temperature 4: 1) O3, 2) Zn / 1) CH2Cl2, -78 deg C, 5 min, 2) AcOH, a) -78 deg C, 5 min, b) rt, 30 min 5: 70 percent / Jones reagent / acetone View Scheme