In a medium skillet over medium heat, toast 1/2 cup barley, stirring constantly, until golden brown and fragrant, about 5 minutes. Set aside.
In a medium saucepan over medium flame, heat oil. Add onion and garlic; cook, stirring, until onion softens, about 2 minutes. Add mushrooms and cook 2 minutes. Stir in toasted barley, remaining 1/4 cup barley, and bay leaf. Add about 1/2 cup simmering broth to barley, stirring until liquid has been absorbed. Continue cooking, adding broth 1/2 cup at a time and stirring, until all liquid has been absorbed and barley is tender, 30 to 35 minutes. Stir in thyme, oregano, pepper and cheese. Remove bay leaf.
To make wine reduction: Meanwhile, in a small saucepan over medium-high heat, bring wine and corn syrup to a boil until reduced to a syrupy consistency, about 20 minutes. Set aside.
To make tenderloin: Sprinkle filets with herbs, salt and pepper. In a large nonstick skillet over medium-high flame, heat oil. Add filets and cook until browned, about 3 minutes on both sides for medium-rare or until desired doneness.
To serve: Press 1/2 cup risotto into a 4-ounce ramekin or custard cup and unmold in center of plate. Repeat to make 3 more molds. Slice each filet horizontally into 4 round medallions. Arrange 1/2 cup steamed vegetables on each plate. Lean beef slices against risotto. Drizzle 1 tablespoon wine reduction over beef, risotto and vegetables.