1: 62 percent / Jones' reagent / acetone / 0.5 h 2: 70 percent / H2 / 5percent Pd-C / ethanol View Scheme

Multi-step reaction with 4 steps 1: 64 percent / Jones reagent / 0.5 h / 0 °C2: 92.9 percent / diethyl ether / 0.17 h / 0 °C3: H2 / 10percent Pd/C / ethanol / Ambient temperature4: Jones reagent / acetone  

Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) room temperature, overnight2: m-CPBA, NaHCO3 / hexane; H2O / 2 h / Ambient temperature3: 1.) Na(PhSe)BH3, 2.) 30percent H2O2, pyridine / 1.) EtOH, reflux, 2 h, 2.) THF, 0 deg C, overnignt; room temperature, 3 h4: 1.) O3, pyridine, 2.) NaBH4 / 1.) MeOH, -78 deg C, 2.) room temperature, 36 h