Answer
The following conversion can be accomplished by adding $OsO_4$, then $H_2O_2$ and then rotating it.
Work Step by Step
Addition of $OsO_4$ and $H_2O_2$ adds two OH across the double bond on the same side. Then rotating the molecules switches the syn addition to anti addition. So if the OH's were wedged, then one of the OH becomes dashed (as shown in the picture).