External application scripts: Apps can also use AppleScripts “externally”—which is to say the user initiates them, typically from the app’s Scripts menu. In Mountain Lion, such scripts will have to be installed in app-specific folders within ~/Library/Application Scripts. By default, applications in Mountain Lion won’t be able to save files to that folder, but users will be able to.
A developer offering a sandboxed app could therefore offer a downloadable set of AppleScripts from its own website. If the user then installs those scripts in the proper location, those scripts can be freely run by the user within the app, with no special entitlements needed. That’s because the user needed to intentionally install those scripts and then to trigger their execution. Because Apple considers the user the ultimate authority over his or her own Mac, the script will be allowed to run.
Developers who worry about whether or not users will install scripts in the right place will be able to create installers that place the scripts correctly; if the user runs and authorizes the installer, that’s treated as permission to put the scripts in the right place.
So, basically, it sounds like someone would have to write an Apple Script that could read the Calibre database and import files to iTunes.
Except, of course, Apple Script has been the lonely stepchild of Apple development for seven or eight years now.
I really like how apparently even the scripts I have in ~/Libraries/Scripts will have to be moved to a new folder in order to continue running.