1: 94 percent / NaBH4 / ethanol 2: bis(tricyclohexylphosphine)benzylideneruthenium(IV)dichlorid 3: H2 / PtO2 4: Bu3P; Py 5: NaH 6: H2O2 / H2O 7: CaCO3 / diphenyl ether / Heating 8: OsO4; NMO / H2O; tetrahydrofuran 9: Py 10: K2CO3 / methanol 11: 61 percent / KOH / methanol 12: 93 percent / HCl / H2O / Heating View Scheme

<b>Multi-step reaction with 11 steps<br /> </b>1: 90 percent / NaBH₄; CeCl₃ / methanol / 0 &deg;C<br />2: H₂ / PtO₂ <br />3: Et₃N<br />4: NaN₃ / dimethylformamide / Heating<br />5: LiAlH₄ / tetrahydrofuran<br />6: K₂CO₃ <br />7: 90 percent / NaH / dimethylformamide<br />8: TBAF / tetrahydrofuran<br />9: Et₃N<br />10: LiI / tetrahydrofuran<br />11: Zn; AcOH / ethanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 10 steps<br /> </b>1: H₂ / PtO₂ <br />2: Et₃N<br />3: NaN₃ / dimethylformamide / Heating<br />4: LiAlH₄ / tetrahydrofuran<br />5: K₂CO₃ <br />6: 90 percent / NaH / dimethylformamide<br />7: TBAF / tetrahydrofuran<br />8: Et₃N<br />9: LiI / tetrahydrofuran<br />10: Zn; AcOH / ethanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 9 steps<br /> </b>1: Et₃N<br />2: NaN₃ / dimethylformamide / Heating<br />3: LiAlH₄ / tetrahydrofuran<br />4: K₂CO₃ <br />5: 90 percent / NaH / dimethylformamide<br />6: TBAF / tetrahydrofuran<br />7: Et₃N<br />8: LiI / tetrahydrofuran<br />9: Zn; AcOH / ethanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: LiAlH₄ / tetrahydrofuran<br />2: K₂CO₃ <br />3: 90 percent / NaH / dimethylformamide<br />4: TBAF / tetrahydrofuran<br />5: Et₃N<br />6: LiI / tetrahydrofuran<br />7: Zn; AcOH / ethanol<br /> <br /> &nbsp;