Preheat oven to 350F.
Grease an 11x7 baking pan with cooking spray or you can also use an 8-inch cake pan or an 8x8 brownie pan.
Arrange the pineapples on the bottom of the prepared pan and add a maraschino cherry in each pineapple hole; set aside.
In a medium bowl, whisk together flour, baking powder, baking soda, and salt; set aside.
In a large bowl, whisk together yogurt, eggs, vanilla, olive oil, and 3/4 cup light brown sugar.
Add flour mixture to the yogurt mixture and mix just until combined and no lumps appear. Set aside.
In a nonstick skillet, melt 4 tablespoons butter over medium-high heat; add the brown sugar and bourbon and stir and cook until sugar is dissolved.
Pour the buttery mixture over the pineapples.
Pour the previously prepared batter over pineapples.
Tap the pan on the counter to settle the batter, and smooth top with an offset spatula.
Bake for 40 to 50 minutes, or until a toothpick inserted in the center comes out clean.
Let stand for 30 minutes in the pan; invert onto a serving platter.
Cut and serve.