For the topping
1/4 cup (56g) unsalted butter, cut into pieces
1/2 cup (52g) light brown sugar, packed
20-ounce can sliced fresh pineapple
For the cake
1/2 cup (113g) unsalted butter, softened
2/3 cup (133g) granulated sugar
2 large eggs, room temperature
1 teaspoon vanilla extract
1 1/2 cups (180g) cake flour
11/2 teaspoons baking powder
1/2 teaspoon salt
Make the topping
Preheat the oven to 180°C. Spray a 9-inch round cake pan generously with non-stick baking spray.
In a medium pot over medium-low heat, stir together butter and brown sugar. Cook the mixture 3 to 4 minutes, until it becomes creamy and bubbles lightly.
Pour the glaze into the bottom of the cake pan. Arrange the sliced pineapple in a single layer over the glaze. Place a cherry in the centre of each pineapple.
Make the cake
In a medium bowl, beat the butter and sugar together with a handheld electric mixer until light and fluffy, about 5 minutes. Beat in the eggs and vanilla until well combined. Sift the flour, baking powder and salt into the butter mixture. Beat on low speed, scraping down the sides of the bowl until well blended. The batter will be thick.
Carefully spoon the batter over the pineapples. Use an offset spatula to spread the batter evenly to the edges.
Bake for 35-40 minutes or until a toothpick inserted into the centre comes out clean. The top will be dark golden brown. If it’s getting too dark, loosely tent the cake with foil.
Cool in the pan for 10 minutes. Run a knife around the edges to loosen the cake from the pan. Invert the cake onto a serving platter. Serve warm with vanilla ice cream.