1: With bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride in dichloromethane T=20°C; 4 h; 2: With pyridinium chlorochromate in dichloromethane 12 h;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: CH₃PPh₃Br; t-BuOK / tetrahydrofuran<br />1.2: 65 percent / NaIO₄ / CH₂Cl₂; H₂O<br />2.1: 84 percent / tetrahydrofuran / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 91 percent / NaH / tetrahydrofuran; dimethylsulfoxide / 3 h / Heating<br />2: 75 percent / dicyclohexylcarbodiimide; CF₃CO₂H; pyridine / DMSO / toluene / 10 h / 20 &deg;C<br />3: 80 percent / tetrahydrofuran / 1 h / -78 - 20 &deg;C<br />4: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 &deg;C<br />5: aq. NaIO₄ / 0.58 h / 0 - 20 &deg;C<br />6: 11.4 g / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 80 percent / tetrahydrofuran / 1 h / -78 - 20 &deg;C<br />2: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 &deg;C<br />3: aq. NaIO₄ / 0.58 h / 0 - 20 &deg;C<br />4: 11.4 g / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 &deg;C<br />2: aq. NaIO₄ / 0.58 h / 0 - 20 &deg;C<br />3: 11.4 g / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: 93 percent / H₂SO₄ / 3 h / 20 &deg;C<br />2.1: CH₃PPh₃Br; t-BuOK / tetrahydrofuran<br />2.2: 65 percent / NaIO₄ / CH₂Cl₂; H₂O<br />3.1: 84 percent / tetrahydrofuran / -78 &deg;C<br /> <br /> &nbsp;