Same problem for me since about two weeks.
Turned out to be a corrupt "recurring" calendar entry in outlook.
So not an Apple problem but a Microsoft problem.
Each time I opened up Outlook 2007 I got a reminder for a meeting that had been replaced/updated by the owner about two weeks earlier. I recall that, apart from noting receiving the update, I afterwards also had to cancel the original calendar, but that that failed (don't remember the error message). Did not give that much more attention as outlook worked.I woudl however get a reminder for the deleted calendar entry when starting outlook, followed by an error message when I tried to dismiss that message: "Cannot open the item for this reminder. Cannot locate recurrence information for this appopintment."
Itunes did not give an sync error message so didn't notice immediately that the calendar sync with outlook had gone wrong. As a result I also did not associate that failure with that specific "recurring" calendar entry.
But after looking on the Internet for a solution I found several references to "corrupted" outlook entries and realized that the "recurring" error message could fit that profile.
So I looked for the above error message and then this link fixed it for me ( I downloaded the mapieditor, closed my outlook, then opened my mailbox via that mapieditor and removed the corrupted calendar entry and restarted outlook with a "cleanreminders" option).
After this itunes properly synced all my new/changed calendar entries again.
http://social.technet.microsoft.com/Forums/ar/exchangesvrgeneral/thread/952774ff -7179-413c-a02c-ec6a864a0259