Windows users have a lot of alternatives to the mainstream media players. However, Mac OS users are not so fortunate. Aside from a couple of minor exceptions, Mac OS is an iTunes-dominated platform. As such, it means support for portable media players that don't have an i at the beginning of their name is scarce.
Instinctiv's Slim, Smart, Sync-Friendly iTunes Alternative
Instinctiv's Slim, Smart, Sync-Friendly iTunes Alternative