Bring a large pot of well-salted water to a boil over high heat.Meanwhile, heat 1 Tbs. of the olive oil with the garlic in a 3-quart saucepan over medium heat. Cook, stirring frequently, until the garlic
is sizzling, about 2 minutes. Add the anchovies and red pepper flakes and cook, stirring frequently, until the garlic is very pale golden, 1 to 2 minutes more. Stir in the tomatoes. Increase the heat to medium high, bring to a boil, and then reduce the heat to medium low and simmer, stirring occasionally, until the sauce is slightly thickened, 8 to 10 minutes.
After adding the tomatoes to the pan, add the pasta to the boiling water and cook according to the package directions until al dente.
When the tomato sauce is ready, add the olives, capers, and oregano and stir. Simmer until just heated through, about 2 minutes. Stir in the remaining 2 Tbs. olive oil and season the sauce to taste with salt and pepper.
When the pasta is ready, reserve 1/2 cup of the cooking water and drain well. Return the pasta to the pot, set it over medium-low heat, pour in the sauce, and toss, adding cooking water as needed for the sauce to coat the pasta. Serve immediately.
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