Preheat oven to 350°F. Pour 1/4 cup melted butter into a 9-inch round baking pan, swirling to evenly coat bottom. Sprinkle brown sugar evenly over butter. To create a flower motif: Arrange pineapple, with rounded edges facing outward, over brown sugar; overlap slices in concentric circle from the center out, to completely cover cake.
In a medium bowl, whisk flour, granulated sugar, baking powder, baking soda, and salt until combined. In a large bowl, whisk remaining 3/4 cup melted butter, the bananas, buttermilk, eggs, and vanilla until well combined. Add flour mixture and stir to combine. Pour cake batter over pineapples, smoothing top with a small offset spatula.
Bake until top is deep golden and a cake tester comes out clean, about 1 hour 15 minutes. Transfer pan to a wire rack to cool 15 minutes. Run a knife around edges of pan, invert cake onto a plate, and let cool completely before serving.
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