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have you reconciled target groups/entitlements. if not reconcile it in the lookup. then run the schedule job "Entitlement List" this will synchronize the entitlements from LKV to ENT_LIST.
This job should kick off Catalog Synchronization job to synchronize the entitlements to Catalog. An entitlement is available when it can be found in Catalog. But if it is not available you can run "Catalog Synchronization job" as well.
make sure you have ticked the Process Roles, Process Application Instances, and Process Entitlements parameters while running Catalog Synchronization job.