I'm not sure WHY I've never thought of making a pineapple upside-down cake with FRESH pineapple before. Maybe it is because ALL of my cookbooks suggest canned pineapple? Maybe it is because canned pineapple is always in the pantry? Maybe it is because I'm not very adventurous? Well, this cake came about due to the rare combination of... "I want to bake something" + "what can I do with this very ripe pineapple?" + "the perfect window of time".
The end result was this pineapple upside-down cake made with FRESH pineapple and it was delicious!! The difference is like night and day!!
Preheat your oven to 350 and cut a parchment paper liner for the bottom of a 9" round cake pan. Spray the pan and parchment paper with a light coating of cooking spray. The parchment paper is not absolutely necessary, but it helps if you have a "sticking" issue with the sweet pineapple glaze (you can use waxed paper in a pinch).
5 tablespoons of melted butter
2/3 cup brown sugar (packed)
3 cups fresh pineapple cut into 1" cubes (see note)
maraschino cherries cut in half
1 1/2 cups all purpose flour
1 1/2 teaspoons baking powder
1/2 teaspoon salt
1/2 teaspoon cinnamon
1/2 cup butter (room temperature)
2/3 cup white sugar
3/4 cup pineapple juice (or milk)
1 teaspoon vanilla
1 teaspoon butter extract
1/2 cup pecans chopped medium-small
Mix melted butter with brown sugar and spread evenly in prepared 9" round cake pan. Set aside.
Cut pineapple into 1" chunks and blot them dry between several thicknesses of paper towel (press on them a little to extract excess juice).
For the batter, cream the butter and sugar until it is really fluffy. Under-beating the butter at this stage will give you a poor quality cake. When it is nice and fluffy, add the eggs (one at a time) and extracts and beat until its fluffy again.
Sift the flour, baking powder and cinnamon into a bowl. Add the flour mixture to the butter mixture in three parts, alternately with the pineapple juice (or milk) starting and ending with the flour. Set aside.
Assembly: Nestle the pineapple, pecans and cherry pieces down into the brown sugar mixture in the cake pan (arrange in pretty fashion because this will show). Pour the cake batter over the top and very gently spread it out.
Bake in 350 oven for 45 to 55 minutes or until a toothpick tests clean (my oven takes exactly 45 minutes). Remove from oven and sit pan on a cooling rack for 15 minutes. After 15 minutes, run a thin bladed knife around the edge of the cake and invert onto a serving plate and peel off the parchment paper. Serve cake warm or at room temperature.
NOTE: Traditionally, pineapple upside-down cake has pretty rings of pineapple with red cherries in the center of each ring. However, when the cake is baked like that, it is hard to eat. You either get a big unmanageable hunk of pineapple on your piece of cake or no pineapple at all (does that make sense?). Instead, I cut the pineapple into very small pieces (almost a dice) and arrange the cherries randomly over the cake. It is much easier to cut, serve and eat (even if it ISN'T traditional). If you use this diced pineapple style, it only takes two cups of diced fruit instead of three.