1: hydrogen / 10percent Pd/C / ethyl acetate 2: 1.) N-chlorosuccinimide, dimethyl sulfide; 3.) triethylamine / 1.) toluene, 0 deg C, 20 min; 2.) toluene, -25 deg C, 2.7h; 3.) r.t., 15 min 3: 93 percent / m-chloroperbenzoic acid / ethyl acetate / 2 h / 35 °C View Scheme

Multi-step reaction with 4 steps 1: H2 / Pd/C-HCl / ethyl acetate2: pyridine / 0 °C3: sodium iodide / acetone / 12 h / Heating4: 24 percent / DBU / toluene / 100 °C  

Multi-step reaction with 8 steps 1: 82 percent / 1.) diisobutylaluminium hydride / 1.) hexane, ether, -78 deg C, 10 min; 2.) MeOH, H2O, r.t., 1 h2: MgSO4 / toluene / 1 h / 0 °C3: imidazole / CH2Cl2 / 69 h / -35 °C4: 1M potassium triethylborohydride / tetrahydrofuran / 1 h / -78 °C5: 91 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / Ambient temperature6: 5.1 mg / K2CO3 / methanol / 0.17 h / Ambient temperature7: 93 percent / CAN / acetonitrile; H2O / 3 h / -10 °C8: 97 percent / imidazole / dimethylformamide / 12 h / Ambient temperature  

With  hydrogen; palladium on activated charcoal in  ethyl acetate