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Preheat oven to 400°F.
Toss Brussels sprouts with 2 teaspoons oil, salt and pepper. Place on a rimmed baking sheet and sprinkle with 1 tablespoon water. Roast for 10 minutes. Stir and sprinkle with 1 tablespoon water. Continue roasting until tender, about 10 minutes more.
Meanwhile, place the remaining 3 teaspoons oil and 5 tablespoons water in a food processor; add sun-dried tomatoes, garlic, pine nuts, vinegar and oregano and process until a rough pesto forms. Stir in Parmesan. Toss the Brussels sprouts with the pesto.