If you want to use TrueType in Java, you will have to copy all needed TrueType fonts to the $JRE/lib/fonts directory. After copying the fonts, make sure that you update the font.dir file of that directory, so that the JRE can find these fonts.
When Pentaho Reporting is used to generate PDF files only, copying the files will not be necessary, iText uses the all fonts of the default font path without using AWT functionality.
The PDF-Target will register all fonts found in the directory "/usr/X11R6/lib/X11/fonts" and all subdirectories. Additionally the directory "/usr/share/fonts" is searched for usable font files.
The iText library uses only TTF and Adobe font files to generate PDF files. If your system stores the fonts in the ResourceFork, Java may not be able to access them.
You can use FONDU (http://fondu.sourceforge.net/) to convert the MacOS fonts into a usable format.
Additionally the MacOS X font directories are searched in the following order:
Any TTF, AFM or PFB file found in these directories will be registered with iText and can be used to create PDF files.
The %WINDIR%/fonts directory is used to search and register the system fonts. The JDK uses all fonts that are available, no additional work is needed.