1: n-butyllithium / tetrahydrofuran; hexane / -78 to 20 deg C 3: 91 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 1.5 h / 75 °C 4: 95 percent / H2 / Lindlar's catalyst, quinoline / hexane / 0.75 h 5: 2.) AG 50W-X4 resin / 1.) iso-octane, 4 h, reflux 2.) methanol, CH2Cl2, 24 h, r.t. 6: 80 percent / diethyl ether / 0.33 h / -78 °C View Scheme

<b>Multi-step reaction with 6 steps<br /> </b>1: 86 percent / tert-butylhydroperoxide, / vanadyl acetyl acetonate / benzene; toluene / 3 h / Ambient temperature<br />2: 88 percent / OsO₄, KIO₄ / tetrahydrofuran; H₂O / 15 h / Ambient temperature<br />3: 89 percent / m-CPBA / CHCl₃; H₂O / 25 h / pH 7.8<br />4: 1.) oxalyl chloride, Me₂SO 2.)Et₃N / 1.) CH₂Cl₂, 15 min, -60 deg C 2.) 0-10 deg C, 5 h<br />5: 95 percent / dimethylaminopyridine, pyridine / 6 h / 25 &deg;C<br />6: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 88 percent / OsO₄, KIO₄ / tetrahydrofuran; H₂O / 15 h / Ambient temperature<br />2: 89 percent / m-CPBA / CHCl₃; H₂O / 25 h / pH 7.8<br />3: 1.) oxalyl chloride, Me₂SO 2.)Et₃N / 1.) CH₂Cl₂, 15 min, -60 deg C 2.) 0-10 deg C, 5 h<br />4: 95 percent / dimethylaminopyridine, pyridine / 6 h / 25 &deg;C<br />5: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 89 percent / m-CPBA / CHCl₃; H₂O / 25 h / pH 7.8<br />2: 1.) oxalyl chloride, Me₂SO 2.)Et₃N / 1.) CH₂Cl₂, 15 min, -60 deg C 2.) 0-10 deg C, 5 h<br />3: 95 percent / dimethylaminopyridine, pyridine / 6 h / 25 &deg;C<br />4: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1.) oxalyl chloride, Me₂SO 2.)Et₃N / 1.) CH₂Cl₂, 15 min, -60 deg C 2.) 0-10 deg C, 5 h<br />2: 95 percent / dimethylaminopyridine, pyridine / 6 h / 25 &deg;C<br />3: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 95 percent / dimethylaminopyridine, pyridine / 6 h / 25 &deg;C<br />2: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 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 />4: 78 percent / KIO₄ / OsO₄ / tetrahydrofuran; H₂O / 5 h / Ambient temperature<br />5: 85 percent / m-CPBA, pH 8 buffer / CHCl₃ / 12 h<br />6: 1) oxalyl chloride, DMSO, 2) NEt₃ / CH₂Cl₂ / 1) -60 deg C, 10 min, 2) room temp., 4 h<br />7: pyridine / DMAP / CH₂Cl₂ / 6 h / Ambient temperature<br />8: 72 percent / Zn, PPh₃, pyridine / 1 h / Ambient temperature<br /> <br /> &nbsp;