Answer
The following conversion can be accomplished by adding $CH_3CO_3H$ and then $H_2O$.
Work Step by Step
The addition of $CH_3CO_3H$ makes an epoxide across the double bond. Then $H_2O$ will attack from the other side on the most substituted carbon. This will open the epoxide breaking the bond and forming $O^-$ on the other carbon. Then the $H^+$ adds to the $O^-$ and makes OH. Since the epoxide blocks one side, the $H_2O$ attacks from the other side. So the addition is anti (one is wedged and other is dashed).