1: 14.6 g / imidazole / dimethylformamide / 16 h / Ambient temperature 2: 84 percent / diethylamine, CuI, bis<triphenylphosphine>palladium(II) acetate / dimethylformamide / 1.5 h / Ambient temperature 3: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 21 h / Ambient temperature 4: 90 percent / H2, quinoline / Lindlar catalyst / methanol; hexane / 0.33 h 5: acetone-d6 / 80.3 °C / var. temp.; kinetics, E(a), ΔG(excit.), ΔH(excit.), ΔS(excit.) View Scheme

<b>Multi-step reaction with 7 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 />7: n-butyllithium / tetrahydrofuran; hexane / -78 to 20 deg C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 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 />6: n-butyllithium / tetrahydrofuran; hexane / -78 to 20 deg C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 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 />5: n-butyllithium / tetrahydrofuran; hexane / -78 to 20 deg C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 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 />4: n-butyllithium / tetrahydrofuran; hexane / -78 to 20 deg C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 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 />3: n-butyllithium / tetrahydrofuran; hexane / -78 to 20 deg C<br /> <br /> &nbsp;