1.1: Dess-Martin periodinane / CH2Cl2 / 3 h / 0 - 20 °C 1.2: 2-methyl-2-butene; NaClO2; NaH2PO4*H2O / tetrahydrofuran; H2O / 5 h / 0 - 20 °C 1.3: HOBt; EDC; triethylamine / CHCl3 / 36 h / 20 °C 2.1: O3 / CH2Cl2; methanol / -78 °C 2.2: 83 percent / Me2S / CH2Cl2; methanol / -78 - 20 °C View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1.1: Cp₂ZrHCl / CH₂Cl₂ / 0.33 h / 20 &deg;C<br />1.2: Me₂Zn / toluene; CH₂Cl₂ / -78 - 0 &deg;C<br />1.3: 64 percent / CH₂Cl₂; toluene / 2 h / 0 &deg;C<br />2.1: 47 percent / TBAF / tetrahydrofuran / 0 - 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: 61 percent / diethyl ether / 20 &deg;C<br />2.1: Cp₂ZrHCl / CH₂Cl₂ / 0.33 h / 20 &deg;C<br />2.2: Me₂Zn / toluene; CH₂Cl₂ / -78 - 0 &deg;C<br />2.3: 64 percent / CH₂Cl₂; toluene / 2 h / 0 &deg;C<br />3.1: 47 percent / TBAF / tetrahydrofuran / 0 - 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: 61 percent / diethyl ether / 20 &deg;C<br />2.1: Cp₂ZrHCl / CH₂Cl₂ / 0.33 h / 20 &deg;C<br />2.2: Me₂Zn / toluene; CH₂Cl₂ / -78 - 0 &deg;C<br />2.3: 64 percent / CH₂Cl₂; toluene / 2 h / 0 &deg;C<br />3.1: 47 percent / TBAF / tetrahydrofuran / 0 - 20 &deg;C<br /> <br /> &nbsp;