1: 99 percent / Me4NB(OAc)3H / acetic acid; acetonitrile / -30 °C 2: 88 percent / 2,6-lutidine / CH2Cl2 / -78 °C 3: 88 percent / Pd(MeCN)2Cl2 / dimethylformamide / 0 °C 4: tetrazole / CH2Cl2 / 0 °C 5: t-BuOOH / CH2Cl2 / 0 °C 6: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 7: 79 percent / aq. HF; pyridine / acetonitrile View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: 98 percent / CeCl₃ / tetrahydrofuran / -50 &deg;C<br />2: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 &deg;C<br />3: 63 percent / NaI; AcOH / 20 &deg;C<br />4: 81 percent / aq. HF; pyridine / acetonitrile / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 &deg;C<br />2: 98 percent / CeCl₃ / tetrahydrofuran / -50 &deg;C<br />3: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 &deg;C<br />4: 63 percent / NaI; AcOH / 20 &deg;C<br />5: 81 percent / aq. HF; pyridine / acetonitrile / 0 &deg;C<br /> <br /> &nbsp;