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Melt butter in small sauce pan and add brown sugar, heavy cream and balsamic vinegar. Bring to boil and then remove from heat. Pour the mixture into the bottom of a baking dish to coat. Shingle the pineapple slices into the sauce in the bottom of the pan. Set aside.
Preheat oven to 350 degrees. Cream the butter and sugar together in a mixer. Add the eggs one at a time and mix well to incorporate. Add the olive oil, sour cream and half and half and mix just until the sour cream disappears. Whisk the flour, baking powder and salt together in a separate bowl and add them to the butter mixture. Mix only until the batter comes together.
Pour batter over the prepared pineapple, spread to the edges, place into the preheated oven and bake until the cake is brown, the sauce is bubbling up the edges, and a toothpick inserted into the middle of the cake comes out clean – 30 to 35 minutes. Let cool slightly then unmold onto a serving plate.
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