http://bugs.winehq.org/show_bug.cgi?id=24255
--- Comment #16 from Chris Pacey haggisman2005_23@hotmail.com 2011-05-03 16:51:07 CDT --- I have traced and found the error. Running iTunes from terminal shows that it cannot use riched20.dll so you need to replace the imaginary wine one with a real one
run in terminal : winetricks riched20
After the command executes iTunes opens correctly