Set your oven to 375º. Cut the pound of bacon in half. Put the brown sugar in a shallow bowl. Take a half a slice of bacon and dredge it through the brown sugar. Put a chunk of pineapple on one end of the bacon slice and roll up. Secure with a toothpick. Lay the bacon pineapple bundles into a pan and bake for at least 25 minutes, or until the bacon looks brown and crispy.