Pineapple Upside-Down Cake

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1 medium fresh pineapple

2 tablespoons sugar + 2/3 cup

1/2 cup (1 stick) unsalted butter

1/2 cup dark brown sugar

1 large egg

2 1/4 cups sifted flour

1 tablespoon baking powder

1/2 teaspoon salt

1 cup milk

2-3 teaspoons vanilla extract

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