1: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) room temperature, overnight 2: m-CPBA, NaHCO3 / hexane; H2O / 2 h / Ambient temperature 3: 1.) Na(PhSe)BH3, 2.) 30percent H2O2, pyridine / 1.) EtOH, reflux, 2 h, 2.) THF, 0 deg C, overnignt; room temperature, 3 h 4: 1.) O3, pyridine, 2.) NaBH4 / 1.) MeOH, -78 deg C, 2.) room temperature, 36 h 5: 62 percent / Jones' reagent / acetone / 0.5 h 6: 70 percent / H2 / 5percent Pd-C / ethanol View Scheme

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