1: 2.04 g / NaBH4 / methanol / 1 h / 20 °C 2: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 3: 96 percent / NaI / butan-2-one / 12 h / Heating 4: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C 5: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / benzene / 6 h / Heating 6: 96 percent / Br2 / diethyl ether / 1 h / -78 °C 7: 53 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 75 °C 8: 100 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C 9: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C 10: NaClO2; NH2SO3H; Na2HPO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 11: Et3N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH2Cl2 / 16 h / 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '10774911', constants.ctx, '0')">lead(IV) acetate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '969212', constants.ctx, '0')">benzene</a> <br />T=20&deg;C;&nbsp;0.75&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: lipase PS (Amano); H₂O / tetrahydrofuran / 480 h / 20 &deg;C<br />2: imidazole / dimethylformamide / 23 h / 0 &deg;C<br />3: 1.90 g / NaOMe / methanol / 2 h / 20 &deg;C<br />4: 96 percent / NaH / tetrahydrofuran / 2 h / 0 &deg;C<br />5: 85 percent / OsO₄; H₂O; Me₃NO*2H₂O / acetone; 2-methyl-propan-2-ol / 20 h / 0 &deg;C<br />6: 89 percent / n-Bu₃SnH; AIBN / toluene / 1 h / Heating<br />7: Pb(OAc)4 / benzene / 0.75 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: imidazole / dimethylformamide / 23 h / 0 &deg;C<br />2: 3.82 g / aq. AcOH / tetrahydrofuran / 5 h / 20 &deg;C<br />3: 96 percent / NaH / tetrahydrofuran / 2 h / 0 &deg;C<br />4: 85 percent / OsO₄; H₂O; Me₃NO*2H₂O / acetone; 2-methyl-propan-2-ol / 20 h / 0 &deg;C<br />5: 89 percent / n-Bu₃SnH; AIBN / toluene / 1 h / Heating<br />6: Pb(OAc)4 / benzene / 0.75 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 100 percent / NaOMe / methanol / 2 h / 20 &deg;C<br />2: imidazole / dimethylformamide / 23 h / 0 &deg;C<br />3: 3.82 g / aq. AcOH / tetrahydrofuran / 5 h / 20 &deg;C<br />4: 96 percent / NaH / tetrahydrofuran / 2 h / 0 &deg;C<br />5: 85 percent / OsO₄; H₂O; Me₃NO*2H₂O / acetone; 2-methyl-propan-2-ol / 20 h / 0 &deg;C<br />6: 89 percent / n-Bu₃SnH; AIBN / toluene / 1 h / Heating<br />7: Pb(OAc)4 / benzene / 0.75 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 96 percent / NaH / tetrahydrofuran / 2 h / 0 &deg;C<br />2: 85 percent / OsO₄; H₂O; Me₃NO*2H₂O / acetone; 2-methyl-propan-2-ol / 20 h / 0 &deg;C<br />3: 89 percent / n-Bu₃SnH; AIBN / toluene / 1 h / Heating<br />4: Pb(OAc)4 / benzene / 0.75 h / 20 &deg;C<br /> <br /> &nbsp;