Ok so I think these would have been better as jumbo cupcakes but they were really good nonetheless. At least with the jumbo tins the entire pineapple circle would have fit whereas with the standards I had to break them up.
I literally cooked the entire thing in a cupcake tin. Most recipes have you make the cupcake first and then add the topping afterwards. But I wanted to try it like a true pineapple upside down. The recipe below is for standard (which gives you a small cake) and in parenthesis is the conversion if you want to make this a jumbo cupcake. I'm sure the jumbo will yield more cake than the standards. If I did these as minis I'd have to add the topping afterwards. Oh, I also added some Amaretto to the cake and topping after it had cooled....yummy!
Pineapple Upside Down Cupcakes
I'm going to give you the box version so you're not spending as much time on them as I did.
1 box spice cake mix or vanilla cake mix (I used spice, was yummy)
1 cup buttermilk
1/2 cup oil (or applesauce)
1 sm can crushed pineapple
2 large can pineapple rings
1 jar maraschino cherries
1 cup shredded coconut
butter (for greasing the tin)
Preheat oven to 350 degrees.
Mix the cake as instructed. Add 1 can of crushed pineapples, along with the juice. Mix on low for 10 seconds.
Mix about 1 cup brown sugar with melted butter (about 1/2 stick). If mixture is watery, add more brown sugar. You want it to be firm but not dry. Wet but not watery.
Grease the cupcake tins - whether it be standard or jumbo. Grease the inside and along the top. Place 1 tablespoon of the brown sugar mix in the bottom of each standard cupcake tin (2 tblspn for jumbo tins). Using a spoon, spread evenly along bottom of tin. Sprinkle about 1 tspn of coconut on top of the brown sugar mix. Take the pineapple and break it up to fit in the standard tins (can place a whole ring intact in the jumbo tins). Take a maraschino cherry and cut in half, place one half in the middle of each pineapple "ring" (can put a whole cherry for the jumbo cupcakes). Now fill the tins about 3/4 way with the cupcake filling for both standard and jumbo.
Place in oven and cook for about 15 minutes (18 - 20 for jumbo) or until toothpick inserted comes out clean of cake. You might get some of the brown sugar topping but that's ok. Allow cupcakes to cook in tins for about 5 minutes. Take about 1 tspn of Amaretto and drizzle over each cake. Afterwards use a flat cookie sheet and place on top of the cupcake tins, holding them together flip them over. Give the cupcake tin a few good hits and they should slide out. Take about 1/2 tspn of Amaretto (if you want) and drizzle over the top of each cake.