Preheat oven to 350°.
Lightly butter or spray with non-stick spray, a 9-inch standard round cake pan.
For the fruit layer, melt the butter in a wide skillet, add the sugar, and stir until it is melted and begins to bubble. Whisk in the pineapple juice, stirring until smooth. Pour this mixture into the bottom of the prepared pan.
In the bottom of the prepared cake pan, arrange the cherries cut side down in a circle, pressing down lightly to adhere. Add a second circle of cherries inside of the first ring. Place pineapple chunks in a circle inside of the cherry rings and another circle of pineapple chunks, if there is room. Place a cherry half (or halves) to fill in the center of the cake.
For the cake, beat the butter with the sugar until fluffy. Beat in the eggs, one at a time, and the vanilla until smooth. Mix the flour with the baking powder and salt. Add the flour alternately with the milk, mixing until just combined. Pour batter over fruit and spread evenly.
Bake for 40 to 45 minutes until golden brown, and a toothpick inserted in the center comes out clean. Let stand 5 minutes and invert onto a sheet pan. Drizzle any lingering caramel over top. Cut into slices and serve topped with whipped cream, if desired.
Nutritional Information. (Per serving without whipped cream) 452.56 calories; 5.23 grams protein; 65.15 grams carbohydrates; 19.75 grams fat (11.66 saturated, 5.75 monounsaturated, 1.04 polyunsaturated); 102.47 mgs cholesterol; 167.40 mgs sodium; 1.47 grams fiber; 45.96 grams sugar; 38 percent calories from fat.