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Preheat the oven to 325 Degrees Fahrenheit or 160 Degrees Celsius.
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Grease and flour 8*3 inch round cake pan.
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Place a saucepan on medium heat and add 1/4 cup butter. To that add brown sugar and mix. Let it simmer on low heat for a minute. Remove and add vanilla extract or rum. Stir. Pour this hot mixture into the prepared pan.
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Drain the pineapple and remove the excess moisture with a paper towel. Arrange the pineapple slices and cherries over the caramel.
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In a bowl, add flour + baking powder + baking soda + salt and sieve or whisk the mixture.
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In another bowl, beat 1/2 cup butter on medium speed with an electric mixer until creamy. Gradually add the sugar, beating until fluffy. Add the eggs, 1 at a time, beating well after each addition. Stir in the vanilla and set aside.
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Add the flour mixture into the egg mixture in three batches, alternately with the buttermilk, beginning and ending with the flour mixture.
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Pour the batter into the pan and bake for 55 minutes to an hour or until a wooden pick inserted in center comes out clean. Let the cake cool in the pan for 10 minutes.
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Invert the cakes onto a wire rack to cool completely.