how to remove photos when itunes advanced option to control photos doesn't?

Inquiry? I am trying to find any ideas on how to remove photos from my 3GS when using the itunes advanced option to control photos doesn't remove them. I have now removed all the photos that I don't want on my iPhone from my MAC iPhoto library and stored the rest of the Photos in some miscellaneous folder. Still phone iPhoto library remains unchanged or at least still includes the 8-900 or so photos I'm trying to reace with a more select 263. Any help greatly appreciated.