my workaround is use a vm windows xp lite version (hacked light version of windows xp) with itunes installed… works like a charm…

for better experience, i mounted my music folder in ubuntu into a shared folder to virtual box and sync itunes library directly… so, to accelerate initializate and finish, i never shutdown the vm… i always use the option "save machine state" (HOST+Q – use first option) that is much faster than shutdown and boot the vm… the disadvantage is this solution occupies 1.3GB of disk storage, but is much better than wine use.

On my other ipod, an old nano 4th gen, i use banshee… very good, works like a charm…