Preheat your oven to 350°F. Grease a 9-inch round cake pan well on the sides.
In a small saucepan, melt the ⅓ cup of butter. Add the brown sugar and pineapple juice and stir until melted together. Do not boil! As soon as it melts, turn it off and pour it into the cake pan. Arrange 7 pineapple slices in a single layer over the brown sugar base. Place a maraschino cherry in the center of each pineapple ring and fill any gaps between the slices with additional cherries if you would like.
In a large bowl or the bowl of a stand mixer, beat½ cup of butter, softened and granulated sugar together until light and fluffy, about 2 to 3 minutes
Add 2 large eggs one at a time, mixing well after each addition. Mix in vanilla extract, pineapple juice, the sourdough discard and whole milk until combined.
In a separate bowl, whisk together all purpose flour, baking powder, baking soda, and salt.
Add the dry ingredients to the wet ingredients and stir until just combined. Do not overmix.
Pour the batter evenly over the pineapple topping in the pan. Bake for 35 to 35 minutes, or until a toothpick inserted in the center comes out clean.
Let the cake rest in the pan for 5 to 10 minutes. Run a knife around the edges, then carefully flip onto a serving plate. Serve warm or at room temperature.