Preheat the oven to 350°F. Spray a non-stick metal 13x9-inch cake pan with baking spray. Set aside.
On the stove top in a small saucepan melt together 1/2 cup butter with 1 1/2 cups packed brown sugar. Stir and cook just until combined then remove from the heat and pour into the bottom of the prepared pan.
Arrange the pineapple rings over the brown sugar mixture then place a maraschino cherry in center of each pineapple slice.
In a large bowl use an electric mixer fitted with the paddle attachment to cream together the remaining 3/4 cup butter, sugar and vanilla extract over medium-high speed.
Add the eggs one at a time beating well after each addition.
In a medium-size separate bowl use a whisk to sift together the cake flour, baking powder and salt.
Lower the speed of the mixer and add the flour mixture to the creamed mixture alternately with the buttermilk beginning and ending with flour. Whip on low speed then increase to medium speed once all is added, mixing just until combined.
Spread cake batter evenly over the pineapple slices. The batter will be thick.
Bake for 50-55 minutes or until a toothpick inserted into the center comes back clean.
Remove from the oven and let cake cool for 5-10 minutes before inverting onto a serving platter. Leave the pan in place for a couple of minutes to allow all of the caramel to drip down the sides of the cake.
Serve at room temperature, warm or chilled with whipped cream or vanilla ice cream.