iTunes on Wine is the closest thing to "native" you'll get but it's not supported very well and you won't get device syncing.
iTunes through VirtualBox is probably going to give you the highest quality experience.. You'll probably be able to use devices (read: iPods, iPhones, iRacks, etc) as you would with a real Windows install. It's just heavy.
I do wonder why you want to run iTunes. If it's just for purchasing, playing and syncing audio files, there are alternatives (Rhythmbox, Banshee, Amarok, MPD+Frontends, etc) that are arguably better and are truly native applications. They just take a little getting used to.
iTunes on Wine is the closest thing to "native" you'll get but it's not supported very well and you won't get device syncing.
iTunes through VirtualBox is probably going to give you the highest quality experience.. You'll probably be able to use devices (read: iPods, iPhones, iRacks, etc) as you would with a real Windows install. It's just heavy.
I do wonder why you want to run iTunes. If it's just for purchasing, playing and syncing audio files, there are alternatives (Rhythmbox, Banshee, Amarok, MPD+Frontends, etc) that are arguably better and are truly native applications. They just take a little getting used to.
Use Banshee to import all meta data from itunes!
In Banshee, Import > Itunes library > navigate to the itunes file - and voa la!
This made my switch from itunes to ubuntu a cinch.
You can use itunes with either wine or PlayonLinux. PlayonLinux is best as performance wise. For installation instruction see http://freshtutorial.com/install-itunes-ubuntu-linux/
Unfortunately, everything I've read says this isn't possible. Your best bet is still a virtual machine or use Rhythmbox.
http://appdb.winehq.org/objectManager.php?sClass=application&iId=1347
As the answer is to any question about Wine, kind of.
You could try, say, Songbird or something. Not really a satisfactory replacement for me, but, it's something.
Meh, I had a hard time finding the right media player for Windows. I won't even try on Ubuntu.
Ubuntu 10.04 should allow you to sync and manage your iPod or iPhone with Rhythmbox.