Preheat oven to 350° F (static) or 325° F (convection).
Lightly oil, then sprinkle the bottoms of one 9 –inch round cake pan or 4 small ramekins with 3-4 tablespoons brown sugar.
Arrange pineapple rings to cover the bottoms of the pans and insert cherries into the centers of the rings or between rings in any decorative pattern. Set aside.
In a large bowl, whisk together all dry ingredients including 1 cup brown sugar, then set aside.
Cut two other pineapple rings into chunks, then purée in a blender or food processor. Remove 2 tablespoons of liquid and set aside. (Use any leftovers in a smoothie or fruity cocktail!)
In a large mixing bowl, beat the eggs until light, approximately 3 minutes.
Add the cream cheese, yogurt, pineapple juice and vanilla extract, mixing until well blended. Slowly add the dry ingredients, mixing an additional 2 minutes after all ingredients are combined. The batter will be smooth, but thin.
Pour the batter into the prepared cake pan(s), completely covering the pineapple rings and sugar.
Bake for 40-45 minutes for 9-inch pan or 30 minutes for small ramekins. Test with a toothpick or cake tester before removing from oven – continue cooking until tester inserted into the cakes comes out clean or with dry crumbs attached.
If the cake has mounded in the center during baking, lay a large knife on the top of the cake pan and saw gently across to evenly cut the bottom of the cake so it sits flat once inverted.
Invert cake(s) onto plates to cool (loosen with a butter knife around the edges) until the cakes drop.
Serve warm or cold.