1: 70 percent / CrO3 / acetic acid / 9 h / Ambient temperature 2: 56 percent / CeCl3, NaBH4 / methanol; tetrahydrofuran / 0.33 h / -10 °C 3: 84 percent / 2,6-lutidine / CH2Cl2 / 20 h / Ambient temperature 4: 90 percent / 2N NaOH / dioxane / 20 h / Ambient temperature 5: 1.) 0.28M LDA, 2.) 3.4 M Red-Al / 1.) THF, -78 deg C, 15 min; 2.) toluene, -20 deg C, 50 min 6: imidazole / dimethylformamide / 1 h / Ambient temperature 7: 85 percent / pyridine, CF3COOH, N,N'-dicyclohexylcabodiimide / benzene; dimethylsulfoxide / 18 h / Ambient temperature 8: 75 percent / 2.5M n-Bu4N(+)F(-) / tetrahydrofuran / 1.) 4 h, 50 degC, 2.) 16 h, RT View Scheme

Multi-step reaction with 4 steps 1: 51 percent / m-CPBA, H5IO6 / 3.5 h / 20 °C / further reagents2: 86 percent / hexane / 2 h / Irradiation3: m-CPBA / CH2Cl2 / 0.83 h / Ambient temperature4: 68 percent / benzene; CH2Cl2 / 0.17 h / -10 °C  

Multi-step reaction with 4 steps 1: benzene / 4 h / Heating2: p-MeC6H4SO3H / acetone / 1 h / Ambient temperature3: NaClO2, NaH2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 12 h / Ambient temperature