To prepare filling, heat 2 teaspoons oil in a medium saucepan over medium heat. Add onion to pan; cook 10 minutes or until tender, stirring occasionally. Add cranberries and next 4 ingredients (through garlic) to pan; cook 10 minutes or until liquid evaporates.
Preheat oven to 375°.
To prepare turkey, combine 1/2 teaspoon salt, cumin, and chile powder in a small bowl. Slice tenderloins lengthwise, cutting to, but not through, other side. Open halves, laying tenderloins flat. Slice each half lengthwise, cutting to, but not through, other side; open flat. Place plastic wrap over tenderloins; pound to 1/2-inch thickness using a meat mallet or small heavy skillet. Sprinkle tenderloins evenly with spice mixture. Spread 1/3 cup filling over each tenderloin. Roll up tenderloins jelly-roll fashion, starting with long sides. Secure at 2-inch intervals with twine. Sprinkle remaining 1/2 teaspoon salt and pepper over tenderloins.
Heat 2 teaspoons olive oil in a large ovenproof nonstick skillet over medium-high heat. Add tenderloins to pan; cook 3 minutes, turning to brown on all sides. Transfer pan to oven. Bake at 375° for 25 minutes or until a thermometer registers 165°. Remove from oven; let stand 10 minutes. Remove twine from tenderloins; slice crosswise into 3/4-inch-thick slices. Garnish with oregano sprigs, if desired.