From the error:
./boomerang-gui: error while loading shared libraries: libQtGui_debug.so.4: cannot open shared object file: No such file or directory
It looks like the boomerang-gui has been linked with debug version of Qt library. So creating a symbolic link like below works.
sudo ln -s /usr/lib/i386-linux-gnu/libQtGui.so.4 /usr/lib/libQtGui_debug.so.4
and
sudo ln -s /usr/lib/i386-linux-gnu/libQtCore.so.4 /usr/lib/libQtCore_debug.so.4
Alternatively, from the ubuntu synaptic package manager you can install debug version of Qt library. (libqt4-dbg)