1: 1.) O3, 2.) Me2S / 1.) CH2Cl2, 2.) -78 deg C 2: acetone / Jones oxidation 3: H2SO4 / Heating View Scheme

1: acetone / Jones oxidation 2: H2SO4 / Heating View Scheme

sulfuric acid 5 h; Heating;

1: p-TsOH / benzene / 16 h / Heating 2: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 10 min, 2.) -78 deg C to room t. 3: Jones reagent / acetone / 0.5 h / 0 °C 4: 87.2 percent / 95 percent H2SO4 / 5 h / Heating View Scheme

1: 1.) Mg / 1.) THF, room t., 2.) THF, room t., 1 h 2: p-TsOH / benzene / 16 h / Heating 3: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 10 min, 2.) -78 deg C to room t. 4: Jones reagent / acetone / 0.5 h / 0 °C 5: 87.2 percent / 95 percent H2SO4 / 5 h / Heating View Scheme

1: benzene / 0 °C 2: 85 percent / ZnI2 / 1,2-dichloro-ethane / Ambient temperature 3: 1.) i-Pr2NLi, HCO2Et, 2.) p-MeC6H4SO2N3, Et3N / 1.) THF, -78 deg C, 2.) CH2Cl2, r.t. 4: Rh2(OAc)4 / benzene / Heating 5: m-ClC6H4CO3H, aq. NaHCO3 / CH2Cl2 / Ambient temperature 6: NiCl2*6H2O, NaBH4 / methanol / Ambient temperature 7: i-Pr2NLi, HMPA / tetrahydrofuran / Ambient temperature 8: LiAlH4 / diethyl ether / Ambient temperature 9: pyridinium chlorochromate / CH2Cl2 / Ambient temperature 10: H2NNH2*H2O, Na / ethane-1,2-diol; bis-(2-hydroxy-ethyl) ether / 185 °C View Scheme