hydrogen; palladium on activated charcoal in methanol

<b>Multi-step reaction with 4 steps<br /> </b>1.1: dicyclohexylborane / hexane; toluene / 0.25 h / 20 &deg;C<br />1.2: (-)-MIB; Et₂Zn / hexane; toluene / -78 &deg;C<br />1.3: 86 percent / hexane; toluene / 2 h / 0 &deg;C<br />2.1: KH / diethyl ether / 0.25 h<br />2.2: 90 percent / diethyl ether; toluene / 2 h / Heating<br />3.1: NaOH / Heating<br />3.2: 84 percent / NaHCO₃ / H₂O<br />4.1: 94 percent / O₃; NaOH / CH₂Cl₂ / 1 h / -78 &deg;C<br /> <br /> &nbsp;