Heat a cast iron skillet over medium high heat. Add 3 teaspoon of olive oil and swirl to coat the skillet.
Add the tomatoes to the hot skillet and cook for 3 minutes, or until the tomatoes begin to blister.
Remove the tomatoes from the heat. Stir in the remaining olive oil, oregano, rosemary, salt, and red pepper flakes. Toss to combine. Allow to stand 5 minutes before serving.