1: tetrabutyl ammonium fluoride / tetrahydrofuran 2: ReOCl3(SMe2)(OPPh3) / benzene / 60 h / 0 °C 3: LiDBB / tetrahydrofuran / 0.25 h / -20 °C 4: 1H-imidazole / N,N-dimethyl-formamide / 40 h / 20 - 50 °C 5: triphenylphosphine hydrobromide / chloroform / 24 h / 20 °C / |Molecular sieve 6: ammonium fluoride-hydrogen fluoride / N,N-dimethyl-formamide; 1-methyl-pyrrolidin-2-one / 144 h / 80 °C View Scheme

<b>Multi-step reaction with 8 steps<br /> </b>1.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 20 &deg;C<br />2.1: sodium methylate / methanol / 20 &deg;C<br />3.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 &deg;C<br />4.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / 0 &deg;C<br />4.2: 3 h<br />5.1: trifluoroacetic acid / dichloromethane; water / 24 h / 20 &deg;C<br />6.1: 2-aminoethyl diphenylborinate; N-ethyl-N,N-diisopropylamine / acetonitrile / 22 h / 20 &deg;C<br />7.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 &deg;C / |Reflux<br />8.1: ReOCl₃(SMe₂)(OPPh₃) / benzene / 72 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 &deg;C / |Reflux<br />2: ReOCl₃(SMe₂)(OPPh₃) / benzene / 72 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 20 &deg;C<br />2.1: sodium methylate / methanol / 20 &deg;C<br />3.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 &deg;C<br />4.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / 0 &deg;C<br />4.2: 3 h<br />5.1: trifluoroacetic acid / dichloromethane; water / 24 h / 20 &deg;C<br />6.1: 2-aminoethyl diphenylborinate; N-ethyl-N,N-diisopropylamine / acetonitrile / 22 h / 20 &deg;C<br />7.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 &deg;C / |Reflux<br />8.1: ReOCl₃(SMe₂)(OPPh₃) / benzene / 72 h / 0 &deg;C<br /> <br /> &nbsp;