In a 12-inch cast-iron skillet, stir together pineapple and brown sugar. Bake for 40 minutes. Remove from oven, and let cool for 30 minutes. Leave oven on.
Transfer pineapple to the container of a blender, and pulse until slightly smooth. Transfer to a large bowl, and stir in coconut.
Cut one biscuit into 8 pieces, and set aside. On a lightly floured surface, arrange remaining biscuits in a rectangle by creating three rows of five, with sides touching. Place biscuit pieces in gaps; and pinch all biscuit edges to seal, creating a solid rectangle. Roll dough to a 16x12-inch rectangle.
Spread pineapple filling onto dough. Starting with one long side, roll up dough into a log. Using a serrated knife, cut log into 8 slices. Place slices in skillet.
Bake until golden brown, 25 to 30 minutes.
In a small bowl, whisk together confectioners’ sugar, condensed milk, 1 tablespoon reserved pineapple juice, and extract until smooth. Drizzle onto warm rolls. Garnish with coconut, if desired. Serve immediately.
Notes
*We used Pillsbury Grands! Homestyle Buttermilk Biscuits.
Recipe by Southern Cast Iron at https://southerncastiron.com/caramelized-pineapple-coconut-rolls/