Ipod failing to sync old podcasts that aren't there

I have a 30GB video iPod. Trying and failing to sync with iTunes on MacBook Pro.
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.
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
iPOD shuffle   Mac OS X (10.4.9)  

What do you mean by old files?   If I am cleaning up a variety of unwanted items I usually put them all into a folder and delete the folder.   Are you talking about Time Machine records?   If so, be very careful how you delete them.

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    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.
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