1: 1.) PdCl2(CH3CN)2, 2.) n-Bu4NF, 3.) aq. K2CO3 2: TEA, DMAP / CH2Cl2 / Ambient temperature 3: PdCl2(CH3CN)2 / CH2Cl2 / 2 h / Ambient temperature 4: 1.) O3, 2.) Me2S / 1.) MeOH. -78 deg C, 2.) MeOH, RT, 5 h 5: NaBH4 / methanol / 3 h / Ambient temperature 6: LiAlH4 / tetrahydrofuran / 2 h / -50 °C 7: p-TsOH / acetone / 10 h / Ambient temperature View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1: 99 percent / 2N aq. HCl / methanol / 3 h / Heating<br />2: imidazole / tetrahydrofuran / 1.5 h / 0 - 20 &deg;C<br />3: TEA, DMAP / CH₂Cl₂ / 0.17 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: imidazole / tetrahydrofuran / 1.5 h / 0 - 20 &deg;C<br />2: TEA, DMAP / CH₂Cl₂ / 0.17 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 1.) NaH / 1.) DMF, 0 deg C, 20 min, 2.) DMF, from 0 deg C to RT, 3 h<br />2: 99 percent / 2N aq. HCl / methanol / 3 h / Heating<br />3: imidazole / tetrahydrofuran / 1.5 h / 0 - 20 &deg;C<br />4: TEA, DMAP / CH₂Cl₂ / 0.17 h / 0 &deg;C<br /> <br /> &nbsp;