1: LiN(i-Pr)2 / THF, 2h ,-78 deg C 2: diethyl ether 3: Bu3SnH, α,α'-azobis(isobutyronitrile) / benzene / 4 h / Ambient temperature 4: diethyl ether; tetrahydrofuran / 0 deg C to r.t., 16 h 5: aq. CH3CO2H / 6 h / Heating 6: 1.) O3 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C 2.) -78 deg C --> RT, 1h 7: 1.) BuLi / 1.) THF, hexane, -78 deg C, 15 min 2. ) 0 deg C, 2 h 8: 100 percent / H2, 10percent aq. HCl / Pearlman's catalyst / ethanol / 15 h / 3000.2 Torr View Scheme