UPDATE: You can see the cherry design got destroyed when I scooped out the batter ~ and there were some bare spots when I flipped it over. The brown sugar/butter mixture formed a caramel layer about 1/2" down from the top. But, to get the "gooey-ness" on top ~ I whisked together about 1 TB caramel ice cream syrup with 1 TB light agave nectar and a heaping TB powdered sugar and brushed it on top (while cake was warm). I didn't want a frosting or glaze, just a translucent gooey top to resemble what it SHOULD have looked like!
My husband is Type 2 diabetic, but doctor took him off his meds about 3 yrs. since his sugar numbers are so good. Still, he doesn't mind sugar-free, so I substituted the white sugar in here with regular white Splenda (not baking blend, which is concentrated). I still used dark brown sugar (b/c I like the caramely flavor it, plus brown Splenda is concentrated) ~ and, of course, the glazed cherries & pineapple have sugar in them. Still, I did replace a full cup of sugar. I used 100% juice pineapple tidbits, but you can use fresh pineapple too (crushed in cans always seems to be in heavy syrup, so you don't want that even if you're not on a sugar-restricted diet). I like the tidbit shapes because the traditional rings are so boring, and harder to cut when you slice the cake (and eat it).
I like glazed cherries better than maraschino cherries (which taste like plastic). I had some left from the Holidays with green pineapple too, so I used the green pineapple in slivers as "leaves" with red cherry halves.
PINEAPPLE UPSIDE DOWN CAKE
1/4 cup (4 TB) butter, unsalted, room temperature
1/2 cup dark brown sugar………………..2 eggs
14 oz crushed pineapple, drained dry
1-1/3 cup all-purpose flour……………….1/4 tsp. ground ginger
2 tsp baking powder………………………1/2 teaspoon salt
1/3 cup shortening (i.e. Crisco ~ I like Buttery Crisco best)
1 cup sugar or 1 cup regular white Splenda (not baking blend)
2/3 cup milk (any kind ~ I like unsweetened vanilla almond, cashew or oat milk)
2 teaspoon vanilla extract
OPTIONAL : glazed (not maraschino) cherry halves
***
Preheat oven to 350 degrees. Spray an 8" or 9" square (or round) pan with non-stick baking spray (containing flour). Put a piece of parchment paper in the bottom of the pan, and spray that too.
Whisk together flour, baking powder, ginger and salt in a bowl. Set aside.
Put butter in a microwave-proof dish or measure and melt (about 40 seconds). Whisk in brown sugar until brown sugar is dissolved. Spread that over the parchment paper in prepared pan and set aside.
Beat together the shortening and white sugar in electric mixer bowl until creamy.
Add in the eggs and vanilla ~ mix well. ** On low ~ mix in half of your dry ingredients. Then add in the milk and finally the remaining dry ingredients Turn speed to med-high and beat for just a minute until smooth.
Press any excess liquid from the pineapple (You may want to turn it onto double-layer paper towels and pat it dry) and then spread over the parchment paper in the pan. If you’re using cherries, arrange the cut halves (rounded side DOWN) however you like, pressing into the pineapple.
Gently spread the batter over the top and smooth the top. Bake about 35-45 minutes (or until a toothpick inserted in center comes out clean).
Let cool in pan about 15-20 minutes, then turn it out onto a platter.Cool completely (don’t forget to take off the parchment paper) and enjoy!
Notes:
(1) You could add some seasonal sprinkles first onto the parchment paper, if you want.
(2) I think square pieces cut from a square pan make a nicer presentation (and easier) than wedges from a round pan ~ but do you have a square cake plate?
(3) I don’t use maraschino cherries because they taste artificial and like plastic.
(4) You can see that I bake/cook for "real" people ~ not perfect and make mistakes. The trick is to be able to somewhat "fix" the mistakes. When you bake or cook for family & friends, they don't care if something isn't perfect (or how great your knife cuts are) ~ just if it TASTES GOOD and that you made it for them!