1: 88 percent / OsO4, KIO4 / tetrahydrofuran; H2O / 15 h / Ambient temperature 2: 89 percent / m-CPBA / CHCl3; H2O / 25 h / pH 7.8 3: 1.) oxalyl chloride, Me2SO 2.)Et3N / 1.) CH2Cl2, 15 min, -60 deg C 2.) 0-10 deg C, 5 h 4: 95 percent / dimethylaminopyridine, pyridine / 6 h / 25 °C 5: 1.) zinc dust, Ph3P 2.) pyridine / 1.) CH2Cl2, 15 min, r.t. 2.) CH2Cl2, 30 min r.t. 6: n-butyllithium / tetrahydrofuran; hexane / -78 to 20 deg C 8: 91 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 1.5 h / 75 °C 9: 95 percent / H2 / Lindlar's catalyst, quinoline / hexane / 0.75 h 10: 2.) AG 50W-X4 resin / 1.) iso-octane, 4 h, reflux 2.) methanol, CH2Cl2, 24 h, r.t. 11: 80 percent / diethyl ether / 0.33 h / -78 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098280', constants.ctx, '0')">tert.-butylhydroperoxide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '14282231', constants.ctx, '0')">bis(acetylacetonate)oxovanadium</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />3&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>2: 1) ICH₂SnBu₃, 2) n-BuLi / 1) THF, 0 deg C, 15 min, room temp. 24 h, 2) THF, -78 deg C to room temp., 20 min.<br />3: 86 percent / t-BuOOH / VO(acac)2 / toluene / 3 h / Ambient temperature<br /> <br /> &nbsp;