The standard procedure of switching to root and then entering
wine iTunesSetup.exe doesn't work. I get a plethora of error messages. I am running Fedora 9. I've done some Googling but haven't gotten very far.
It appears that the newest version of iTunes isn't compatible with wine.
Only iTunes 7.x actually works. Wine Application Database
I don't know about iTunes under Wine. But you have a few great alternatives on GNU/Linux.
I personally use Amarok under Debian with my iPod, but you may also try: