I hate to be 'that guy', but have you tried wine? Wine typically has very good compatibility with popular applications like iTunes. Okay, I just checked appdb

I hate to be 'that guy', but have you tried wine? Wine typically has very good compatibility with popular applications like iTunes. Okay, I just checked appdb and it kinda works. (May be worth trying a prerelease of wine). Otherwise, ubuntu should have built in iPod support (I am assuming that's what you need iTunes for), and if not, I guarantee there's a way to get it working on the internet/wiki somewhere.