Preheat oven to 425 degrees F.
On a rimmed baking sheet combine eggplant, ¼ cup olive oil and half the oregano, salt, red pepper flakes, and pepper. Toss to combine. Bake eggplant for 20 minutes, to.
Cook pasta according to the package directions, strain, and set aside.
Meanwhile, in a skillet over medium-high heat, add 1 tablespoon of olive oil. When heated, add the diced onion and sauté for 5 minutes.
Add the garlic, the remaining oregano, salt, pepper, red pepper flakes, and tomato paste to the skillet. Cook for 1 minute, stirring continuously.
Then add the canned tomatoes and stir to combine. Bring to a low boil, then reduce to a simmer. Allow to simmer for 10 minutes, stirring occasionally until the sauce has thickend and is jam-like.
Add the eggplant to the tomato sauce and stir to combine.
Add the pasta to the sauce. Stir to combine and top with grated cheese and basil.
Serve immediately.