My dear old Europa (before she died
) had an Ultegra triple crankset - 50/39/30 - just standard Shimano fare.
The front derailleur is Ultegra but from about a decade ago.
The rear cassette is a 9 speed 11-32
At one point, I took off the 30 and fitted a 26.
I already had a Shimano mtb rear dr (maybe an XT? but I don't remember) - this was replaced with a 105 rear dr (medium reach from memory) when the old one packed up.
I NEVER had troubles with this. I needed the 26x32 because my ride home featured a 10%+ climb. Equally, going the other way, I had to ride down that slope in the same lane as the traffic which is where the 50x11 was useful as I could maintain the 70 km/hr the cars were doing... despite the 60 km/hr speed limit.