5 Pd(II)/C(eggshell); ammonium formate in methanol 6 h; Reflux;

1: 95 percent / p-TsOH / dimethylformamide / 24 h / 20 °C 2: 90 percent / NaH / dimethylformamide / 20 h / 20 °C 3: 82 percent / aq. HOAc / 1.5 h / 80 °C 4: 39 percent / 4-dimethylaminopyridine; EDCI / CH2Cl2 / 1 h / 20 °C 5: 28 percent / 1,4-cyclohexadiene / Pd/C / ethanol; dimethylformamide / 10 h / 40 °C View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: 60 percent / BF₃*Et₂O / CH₂Cl₂ / 6 h / 20 &deg;C<br />2: 100 percent / NaOMe; MeOH / 4 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 76 percent / DBU / CH₂Cl₂ / 0.5 h / 20 &deg;C<br />2: 34 percent / TMDSOTf / diethyl ether / 1 h / 20 &deg;C<br />3: 100 percent / NaOMe; MeOH / 4 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 85 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating<br />2: 62 percent / trimethylsilyl triflate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -35 &deg;C<br />3: NaOCH₃ / methanol / 5 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 60 percent / BF₃*Et₂O / CH₂Cl₂ / 6 h / 20 &deg;C<br />2: 100 percent / NaOMe; MeOH / 4 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 92.2 percent / K₂CO₃ / acetone / 10 h / Heating<br />2: 85 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating<br />3: 62 percent / trimethylsilyl triflate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -35 &deg;C<br />4: NaOCH₃ / methanol / 5 h<br /> <br /> &nbsp;