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Slice the pineapple into seven ½-inch-thick rounds. Quarter 2 rounds, trimming and discarding the core. In a food processor, puree the quartered pineapple slices, oil, brown sugar, garlic, chipotles and adobo, cumin, ancho powder and 2 teaspoons salt until smooth, about 1 minute. Pour ½ cup into a baking dish; pour the rest into a medium bowl and stir in 1 tablespoon of the lime juice. Set both aside.
Place the tenderloin halves between 2 large sheets of plastic wrap. Using a meat mallet, pound the pork to an even ½-inch thickness. Season both sides of each piece with salt and pepper, place in the baking dish and turn to coat with the puree. Let marinate at room temperature for 15 minutes.
Meanwhile, heat the broiler to high with a rack about 4 inches from the element. Line a rimmed baking sheet with extra-wide foil and mist with cooking spray. Arrange the 5 remaining pineapple slices in a single layer on the prepared baking sheet. Brush the slices with oil and sprinkle with salt and pepper, then broil until charred in spots, 7 to 10 minutes. Transfer the pineapple to a cutting board and set aside; reserve the baking sheet.
Transfer the tenderloin halves to the same baking sheet and broil until charred in spots and the center reaches 140°F or is just barely pink when cut, 7 to 10 minutes. Let rest for 5 minutes.
While the pork rests, chop the pineapple into rough ½-inch cubes, discarding the core. Transfer to a small bowl and stir in the cilantro and the remaining 1 tablespoon lime juice, then taste and season with salt and pepper.
Cut the pork crosswise into thin slices on the diagonal. Transfer to a medium bowl, then stir in any accumulated pork juices along with 3 tablespoons of the reserved pineapple puree. Serve the pork, chopped pineapple and remaining pineapple puree with the tortillas, chopped onion and lime wedges.