Why isn't iTunes working for me?
I've also tried this, it didn't work for me.
iTunes was rated as Silver on the Winehq website, with few known reports of it working properly. http://appdb.winehq.org/objectManager.php?sClass=application&iId=1347
I use banshee, it's simple, lightweight, and all around in my opinion, it's better than iTunes. It also allows you to Sync media to your iPod or iPhone, but with limited functionality.
Hope this helps. :)