I just tried both Wine 2.0.1 (stable) and 2.9 (Devel) on a MacBook Air running Sierra 10.12.5, but I was not able to get past the main menu except on my first try, due to the mouse cursor being trapped in a large square in roughly the top 1/4 of the screen. The first try I was able to get all the way to the menu for the first mission of the training, but I wasn't able to launch it due to the second disk not being mounted. I'll keep trying, since I really want to get this to work.