Prepare 2 JUMBO cupcake pans by greasing the molds, and then lining just the bottoms with paper liners. I used Jumbo cupcake liners, and cut them down so the liner just fills the bottom (and up the side just a bit). The liner will just help keep the pineapple and glaze in tact as you remove the cakes from the pan.
Prepare the pineapple slices by cutting out a notch of pineapple (as pictured above). This allows the pineapple to sit nicely in the bottom of the cupcake pan. Cut one pineapple slice and then place it in your pan to get an idea of the size piece you need to remove.
Prepare the brown sugar glaze by combining the butter, corn syrup and brown sugar in a small saucepan. Heat until the butter and sugar are melted, and the mixture is smooth. Set aside to cool.
Prepare the cake batter. In a large bowl add the flour, baking powder, baking soda and salt. Whisk to combine, then set aside.
In the bowl of an electric mixer, add eggs and beat 15 seconds. Add the sugar, and continue to beat until the mixture thickens and is a light in color.
While mixing on low speed, add the oil and vanilla and mix until well blended. Add sour cream, and mix to combine.
Slowly add the flour mixture and mix just until the flour is fully incorporated.
Assemble cakes for baking by adding 1-1/2 tablespoons of the brown sugar mixture to the bottom of each (lined) cupcake mold. Top glaze with a slice of pineapple and half of a maraschino cherry.
Pour (or scoop) the cake batter on top of each pineapple slice, filling each cupcake mold 2/3 - 3/4 full (do your best to evenly divide the batter between each cupcake).
Bake cupcakes in a preheated 350*F oven for about 25 minutes (or until a toothpick inserted in the center of a cake comes out clean, or with a few moist crumbs).
Allow cakes to cool about 5 minutes, then run a knife along the edges of each cake to loosen it from the pan. Flip over the entire pan, onto a baking sheet. Remove the paper liner, and serve.
Cakes can be served warm, or at room temperature.