1: 1.) EtMgBr 2.) CuCl / 1.) THF, reflux, 2 h 2.) THF, HMPA, 0 deg C 2: 3.5 M H2SO4 / acetone / 5 h / 25 °C 3: CrO3, 3.5 M H2SO4 / acetone / 1.) 0 deg C, 1 h 2.) 20 deg C, 4 h 4: NaBH4 / ethanol / -20 - 0 °C 5: 73 percent / H2 / P-2 nickel View Scheme

<b>Multi-step reaction with 6 steps<br /> </b>1: 44 percent / hexametapol / 0.08 h / 205 &deg;C<br />2: 65 percent / O₂, PdCl₂, CuCl / tetrahydrofuran; H₂O / 6 h / 60 &deg;C<br />3: 90 percent / pyridinium tosylate / benzene / 32 h / Heating<br />4: 1.) Li, NH₃, FeCl₃ / 1.) -37 deg C, 3 h, 2.) Et₂O, -37 deg C, 4 h<br />5: 9.21 g / KOH / diethyl ether / 0.5 h / 0 &deg;C<br />6: NaBr / dimethylformamide / 2 h / 65 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: NaBr / dimethylformamide / 2 h / 65 &deg;C<br />2: 1.) Li, NH₃, FeCl₃ / 1.) -37 deg C, 3 h, 2.) Et₂O, -37 deg C, 4 h<br />3: 9.21 g / KOH / diethyl ether / 0.5 h / 0 &deg;C<br />4: NaBr / dimethylformamide / 2 h / 65 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 65 percent / O₂, PdCl₂, CuCl / tetrahydrofuran; H₂O / 6 h / 60 &deg;C<br />2: 90 percent / pyridinium tosylate / benzene / 32 h / Heating<br />3: 1.) Li, NH₃, FeCl₃ / 1.) -37 deg C, 3 h, 2.) Et₂O, -37 deg C, 4 h<br />4: 9.21 g / KOH / diethyl ether / 0.5 h / 0 &deg;C<br />5: NaBr / dimethylformamide / 2 h / 65 &deg;C<br /> <br /> &nbsp;