In a medium (10-inch) pot or Dutch oven, such as Le Creuset, warm the olive oil over medium-low heat. Add the garlic and cook for 10 to 12 minutes, tossing occasionally, until the garlic has softened and is lightly browned.
Meanwhile, drain the tomatoes, place them in a food processor fitted with the steel blade, and pulse until they're roughly chopped. With a slotted spoon, transfer the garlic to the food processor and pulse again to chop the garlic. Pour the tomato mixture into the pot with the olive oil, add the fennel, red pepper flakes, red wine, 1 tablespoon salt, and 1 teaspoon black pepper. Bring to a boil, lower the heat, and simmer for 30 minutes. Stir in the basil, taste for seasonings (it will be very spicy!), and keep warm over very low heat.
Meanwhile, bring a large pot of water to a full boil. Add 2 tablespoons kosher salt and the penne and cook according to the directions of the package.
Two minutes before the pasta is al dente, using a wire or spider strainer, lift the pasta out of the boiling water and add it to the sauce, along with 1/4 cup of the pasta water. Simmer for 2 to 3 minutes, until the pasta is al dente. Spoon the pasta into low shallow bowls, sprinkle with extra basil and Parmesan cheese, and serve hot.