1.1: t-BuOCl / CH2Cl2 / 10 h / 20 °C / Heating; in dark 1.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C 2.1: H2 / 10 percent Pd-C / methanol / 40 h / 20 °C 3.1: NaBH4 / H2O; acetonitrile / 0.25 h View Scheme

1.1: t-BuOCl / CH2Cl2 / 10 h / 20 °C / Heating; in dark 1.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C 2.1: H2 / 10 percent Pd-C / methanol / 40 h / 20 °C View Scheme

<b>Multi-step reaction with 5 steps<br /> </b>1: BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />2: 84 percent / NMO / OsO₄ / H₂O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating<br />3: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />4: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath<br />5: DCC / tetrahydrofuran / 6 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 84 percent / NMO / OsO₄ / H₂O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating<br />2: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />3: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath<br />4: DCC / tetrahydrofuran / 6 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />2: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath<br />3: DCC / tetrahydrofuran / 6 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath<br />2: DCC / tetrahydrofuran / 6 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />2: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath<br />3: DCC / tetrahydrofuran / 6 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: Et₃N / CH₂Cl₂ / 1 h / 20 &deg;C<br />2: Jones reagent / acetone / 0.25 h / at ice bath<br />3: tetrahydrofuran / 2 h / -78 - 20 &deg;C<br />4: BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />5: 84 percent / NMO / OsO₄ / H₂O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating<br />6: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />7: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath<br />8: DCC / tetrahydrofuran / 6 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: tetrahydrofuran / 2 h / -78 - 20 &deg;C<br />2: BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />3: 84 percent / NMO / OsO₄ / H₂O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating<br />4: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />5: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath<br />6: DCC / tetrahydrofuran / 6 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: Et₃N / CH₂Cl₂ / 1 h / 20 &deg;C<br />2: Jones reagent / acetone / 0.25 h / at ice bath<br />3: tetrahydrofuran / 2 h / -78 - 20 &deg;C<br />4: BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />5: 84 percent / NMO / OsO₄ / H₂O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating<br />6: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />7: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath<br />8: DCC / tetrahydrofuran / 6 h / Heating<br /> <br /> &nbsp;