ITunes trying to sync old podcasts (and failing!)

I have a 30GB video iPod. Trying and it failing to sync with iTunes on MacBook Pro. Same problems happen with new shuffle so would seem to be an iTunes problem.
First of all it says some items in the iTunes library including xxxx were not copied because they could not be found. It then gives a list of OLD podcasts that I can't find in iTunes or in finder.
Is there a corrupt file that tells iTunes to look for old podcasts to sync with?
It gets so far and then says "attempting to copy to the disk yyyyyy failed. The disc could not be read from or written to.
However it is NOT an iPod problem. The same iPod will sync fine with iTunes on a windows PC and a Shuffle suffers the same problem with this MacBook Pro.
TIA
Dermot

Welcome to the Palm Support Community Emily, but I'm at a loss as to what you are asking... 
What exactly is "the new operating system"?   Windows 7?   If so, what bit depth is it?  32bit or 64bit?
What is "that file" you're referring to that you think is a .dll?   Your Contacts and Calendar data?
What is "Outlook 7"?   Microsoft Outlook 2007?
If indeed you've just obtained Windows 7, and it's the 64bit version, there is a way to sync the TX via a wireless method - either BlueTooth or Wifi.
Please read the thread I wrote on "How to sync the TX and Vista64" at the top of this section.  It's very similar to Windows 7.
WyreNut
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