Wrap the whole head of garlic (unpeeled) in aluminium foil and place in a baking tin.
Bake in the preheated oven for 50 minutes or until tender. Once cooked, remove from oven and let it cool for a little bit. Squeeze each garlic clove to obtain the creamy pulp of the garlic. Transfer to a plate and chop a little bit for a more minced texture.
In a large pot of boiling salted water, cook pasta until just al dente, according to the instructions on the packet. Drain well and toss with 1 tablespoon of olive oil.
In a medium saucepan, heat the remaining olive oil and cook and stir chopped fresh tomatoes and sun-dried tomatoes for about 5 minutes. Add roasted garlic and season with salt, pepper and oregano.
Add cooked pasta, toss well and serve in individual bowls. Sprinkle with Parmesan cheese.