http://tomcat.apache.org/tomcat-5.0-doc/manager-howto.html#Deploy%20A%20New%20Application%20Remotely Executing Manager Commands With Ant Copy the file server/lib/catalina-ant.jar from your Tomcat 5 installation into Ant's library directory ($ANT_HOME/lib).
As noted in http://gentoo-wiki.com/HOWTO_Apache_Ant_and_Jakarta_Tomcat you can use a symbolic link
/opt/tomcat5 needs permissions fixing as well drwxr-x--- 9 tomcat tomcat 264 Mar 23 12:57 tomcat5/
I believe that it is better, in general, for a project/package to manage it's own ant tasks (ie include in lib directory, and declare the taskdefs). Additionally, tomcat is slotted. So, unless the catalina-ant.jars are named differently between the different slots and live under different package hierachies, there's going to be problems with this approach.
Tomcat 5.0.x is very old now, and upstream (Tomcat Devs) highly recommend against anyone installing or using this version. Please use Tomcat 5.5.x in java-experimental overlay. http://www.gentoo.org/proj/en/java/experimental.xml Tomcat 5.0.x ebuilds will be masked soon and eventually removed all together. Tomcat 5.5.x should be added to portage within a month or so. Just after migration to new java system is complete. Permissions and many other issues have been address in 5.5.x ebuild in java-experimental overlay.
I'm sticking by my initial position in comment #3.
