Preheat your oven to 450°F. Line a baking sheet with foil and lightly coat it with cooking spray.
Arrange the tomatoes cut-side up on the baking sheet. Drizzle with olive oil, then sprinkle with oregano, salt, and pepper. Roast for 10 minutes, add minced garlic, and roast for another 5-10 minutes until soft and slightly caramelized.
On another baking sheet, arrange sliced portobello mushrooms. Toss with olive oil, rosemary, salt, and pepper. Roast for 10 minutes, stir in garlic, then roast another 5-7 minutes until tender and slightly browned.
Meanwhile, boil a large pot of salted water. Cook the whole wheat rotini according to package directions and drain.
In a large skillet, heat 2 tablespoons of olive oil over medium heat. Add garlic and sauté for 1 minute until fragrant. Pour in white wine and a pinch of red pepper flakes, letting it simmer for 2-3 minutes to reduce.
Add the drained pasta, roasted tomatoes, mushrooms, parsley, and Parmesan to the skillet. Toss until evenly combined and heated through. Adjust salt and pepper to taste.
Serve warm with additional Parmesan on top, if desired.