1.1: dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / |Inert atmosphere 1.2: 0.25 h / 20 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / |Inert atmosphere 2.2: 48 h / 0 °C / |Inert atmosphere 3.1: sulfuric acid / tetrahydrofuran; water / 12 h / |Reflux 4.1: sodium tetrahydroborate / methanol / 1 h / 0 - 25 °C View Scheme

<b>Multi-step reaction with 8 steps<br /> </b>1: iodine / acetonitrile / 24 h / 0 &deg;C / |Inert atmosphere; |Darkness<br />2: sodium carbonate / methanol / |Inert atmosphere; |Reflux<br />3: (S,S)-(salen)Co(OAc) complex; water / 12 h / 0 - 25 &deg;C / |Resolution of racemate<br />4: triethylamine / dichloromethane / 1 h / 0 &deg;C / |Inert atmosphere<br />5: sodium azide / N,N-dimethyl-formamide / 8 h / 80 &deg;C<br />6: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 25 &deg;C<br />7: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 &deg;C / |Inert atmosphere; |Reflux<br />8: sodium carbonate / dichloromethane; water / 8 h / |Reflux<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: sodium azide / N,N-dimethyl-formamide / 8 h / 80 &deg;C<br />2: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 25 &deg;C<br />3: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 &deg;C / |Inert atmosphere; |Reflux<br />4: sodium carbonate / dichloromethane; water / 8 h / |Reflux<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 25 &deg;C<br />2: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 &deg;C / |Inert atmosphere; |Reflux<br />3: sodium carbonate / dichloromethane; water / 8 h / |Reflux<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 &deg;C / |Inert atmosphere; |Reflux<br />2: sodium carbonate / dichloromethane; water / 8 h / |Reflux<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: triethylamine / dichloromethane / 1 h / 0 &deg;C / |Inert atmosphere<br />2: sodium azide / N,N-dimethyl-formamide / 8 h / 80 &deg;C<br />3: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 25 &deg;C<br />4: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 &deg;C / |Inert atmosphere; |Reflux<br />5: sodium carbonate / dichloromethane; water / 8 h / |Reflux<br /> <br /> &nbsp;