I found the original recipe for this from the cook's illustrated cookbook after being asked to bring dessert to my best friends for our Christmas dinner, I made a couple of changes to fit my tastes. My best friends Dad loves pineapple upside down cake from scratch, I was so thrilled when this cake came out just right not to dry, not soggy and a real pineapple flavor.
Adjust oven rack to lower-middle position and heat oven to 350 degrees.
Grease 9-inch round cake pan, line with parchment paper, grease parchment, and flour pan.
For the topping: Cook pineapple and brown sugar in 10-inch skillet over medium heat until pineapple is translucent and has light brown hue, 15 to 18 minutes, stirring occasionally during first 5 minutes.
Transfer fruit and juices to a fine strainer set over a small bowl (you should have about 2 cups cooked fruit).
Return juices to skillet and simmer over medium heat until thickened, begining to darken, and mixture forms large bubbles, 6 to 8 minutes, adding any more juices released by fruit to skillet after about 4 minutes. (Pineapple will continue to release liquid as it sits; do not add this liquid to already-reduced juice mixture.)
Off heat whisk in butter and almond extract. Pour carmel mixture into prepared cake pan and set aside while preparing cake.
For the cake: Whisk flour,baking powder and salt in medium bowl.
Using stand mixer fitted with paddle, beat butter and sugar on medium-high until pale and fluffy, about 3 minutes.
Reduce speed to medium, add almond extract, and beat to combine.
Increase speed to medium-high, add eggs and egg white, 1 at atime, and beat until combined.
Reduce speed to low and add flour in 3 additions, alternating with 2 additions of milk, scraping down bowl as needed (batter will be thick. Give batter a final stir by hand.
Add Cherry halves around cake pan in circle in carmel. Working quickly, distribute drained pineapple in cake pan in even layer, gently pressing fruit into carmel.
Using rubber spatula, drop mounds of batter over fruit, then spread batter over fruit and to sides of pan in even layer. Gently tap pan on counter to release air bubbles.
Bake cake until golden brown and toothpick inserted in center comes out clean, 45 to 50 minutes. Cool 10 minutes on wire rack, then place inverted serving platter over cake pan. Invert cake pan and platter together, then remove pan. Let cool to room temperature, about 2 hours, and serve.