Trouble Synching

When I identify the music in my library kept on my iMac that I want to put on my iPhone 4 and check the playlists, artists, albums, and genres only a small number of the checked items are actually copied onto the phone.  What am I doing wrong?
Across from the "Sync Music" headiing on the iTunes Music page is a number that increases as I add (check) more music.  Just now, I wanted to sync 1,182 songs onto the phone.  The blue ("audio") portion of the "Capacity" bar at the bottom of the page showed 0.47 GB/102 songs/11.5 hours.  When I synced the phone, only 102 songs were copied.   I don't understand why all the checked items weren't copied.
Other factors:  It is a 16 GB phone; I just updated iTunes, it's running software version 4.3.5, the Capacity bar showed that the phone still has 5.8 GB free; and under "Options" on "Summary" page, the only box checked is "Sync only checked sonfgs and videos."
Can anyone help?

Hi and Welcome to the Community!
With that exact error code, I find no useful documentation...you might have better luck:
http://btsc.webapps.blackberry.com/btsc/microsites/microsite.do
Otherwise, I suggest this thread:
http://supportforums.blackberry.com/t5/Desktop-Software-for-PC/Cleanly-quot-Starting-Over-quot-with-...
It starts with a process for cleanly starting over, and there is some discussion, and there is also a post (15) with links to older Desktop Software versions, if those are needed. Note that this is not, by any means, guaranteed to work...but it has worked for many to resolve issues they are having.
Good luck!
Occam's Razor nearly always applies when troubleshooting technology issues!
If anyone has been helpful to you, please show your appreciation by clicking the button inside of their post. Please click here and read, along with the threads to which it links, for helpful information to guide you as you proceed. I always recommend that you treat your BlackBerry like any other computing device, including using a regular backup schedule...click here for an article with instructions.
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