Place olive oil and garlic in a large saucepan. Heat over medium hear until the garlic begins to sizzle, but not brown ,about 30 seconds. Add the olives, capers, and 1/4 teaspoons of red pepper flakes. Add the puréed and crushed tomatoes. Bring to a boil, reduce heat, and simmer for 15 minutes. Add the basil sprig, the remaining 1/4 teaspoons red pepper flakes, and the oregano, and cook for an additional 10 minutes.
Meanwhile, generously salt the boiling water. Add the pasta, and cook until tender but still firm. Set the timer for 2 minutes less than the package instructions specify, and taste for doneness. Drain the pasta and toss with the sauce. Serve with additional red peper flakes, grated Parmesan cheese, and freshly torn basil leaves.