According to WineHQ's application database (see here
), at least some versions of iTunes might run on Wine.
Though I consider iTunes trash software, simply because it has never worked without problems on me
The other available software works perfectly with the iPod I own, and that's enough (software like Amarok, GTKpod or one of the Windows things like Winamp plugin).
: whenever Wine is in question, don't expect anything to run on it. There is no guarantee, and from personal experience I can tell that if a program does run on one Wine version, it might not run on another -- even if the "another" version was newer. Some apps run perfectly fine, others don't run at all, and some may crash at unexpected places. If you really need the Windows programs, buy a legal copy of Windows (XP is good) and either install it as a virtual operating system or just get it some hardware of it's own, preferrably new enough for it to run fast enough for your nerves.