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1
Preheat the oven to 350F.
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2
In a flameproof 9-inch cake pan, melt 1/3 cup of the butter over low heat.
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3
Sprinkle the brown sugar evenly over the butter and cook, stirring, until the sugar and butter are blended and there are no pools of melted batter, 2 to 4 minutes.
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4
Arrange the pineapple on top of the caramel.
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5
Decorate with cherries if desired, placing them in the center of each pineapple slice.
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6
Set the pan aside.
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7
In the work bowl of an electric stand mixer fitted with the paddle attachment, or in a large mixing bowl with a handheld mixer, place the flour, sugar, baking powder, and salt and mix on low speed until well combined.
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8
Add the remaining 1/3 cup of butter along with the milk and vanilla.
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9
Beat on medium speed for 2 minutes.
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10
Scrape down the sides of the bowl.
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11
Add the egg and beat on medium speed for 2 minutes.
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12
Pour the batter over the pineapple.
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13
Bake until the cake is golden brown and a toothpick inserted in the center comes out clean, 40 to 50 minutes.
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14
Remove the pan from the oven and carefully tilt it in all directions to release the cake from the sides of the pan.
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15
Let cool in the pan for about 3 minutes.
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16
Turn the pan over onto a serving plate and let stand for 2 to 3 minutes.
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17
Carefully lift the pan off the cake.
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18
Use a spatula to remove any fruit that is stuck to the pan and place it on the cake.
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19
Serve warm or at room temperature.
