1: di-isopropyl azodicarboxylate, Ph3P / tetrahydrofuran / 12 h / -20 °C 2: hydrazine / ethanol / 6 h / Heating 3: Et3N / CH2Cl2 4: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C 5: Et3N / CH2Cl2 6: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature 7: K2CO3 / methanol 8: CF3CO2H, anisole View Scheme

1: di-isopropyl azodicarboxylate, Ph3P / tetrahydrofuran / 12 h / -20 °C 2: hydrazine / ethanol / 6 h / Heating 3: Et3N / CH2Cl2 4: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C 5: Et3N / CH2Cl2 6: K2CO3 / methanol 7: H2 / Pd(OH)2/C / methanol View Scheme

1: di-isopropyl azodicarboxylate, Ph3P / tetrahydrofuran / 12 h / -20 °C 2: hydrazine / ethanol / 6 h / Heating 3: Et3N / CH2Cl2 4: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C 5: Et3N / CH2Cl2 6: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature 7: K2CO3 / methanol View Scheme

1.1: NaH / tetrahydrofuran / 0.5 h / Heating 1.2: 81 percent / tetrahydrofuran / Heating 2.1: [Cl2(PCy3)2Ru=CHPh] / toluene / 25 °C 2.2: NaOH; 2-propanol; [Cl2(PCy3)2Ru=CHPh] / toluene / 2 h / 110 °C View Scheme