Pineapple Topping
1 medium fresh pineapple (about 4 pounds), peeled and cored and cut in to 1/4-inch chunks
1 cup (7 ounces) firmly packed dark brown sugar
3 tablespoons unsalted butter
1 teaspoon vanilla extract
Cake
1 1/2 cups (7 1/2 ounces) unbleached all-purpose flour
1 1/2 teaspoons baking powder
1/2 teaspoon table salt
8 tablespoons unsalted butter (1 stick), softened but still cool
3/4 cup (5 1/4 ounces) granulated sugar
1 teaspoon vanilla extract
2 large eggs at room temperature
1 egg white at room temperature
1/3 cup whole milk at room temperature
Lightly spray 9-inch round, 2-inch deep cake pan with nonstick cooking spray; set aside.
For the pineapple topping: Combine pineapple and brown sugar in
10-inch skillet; cook over medium heat, stirring occasionally during
first 5 minutes, until pineapple is translucent and has light brown hue,
15 to 18 minutes. Empty fruit and juices into mesh strainer or colander
set over medium bowl. Return juices to skillet, leaving pineapple in
strainer (you should have about 2 cups cooked fruit). Simmer juices over
medium heat until thickened, beginning to darken, and mixture forms
large bubbles, 6 to 8 minutes, adding any more juices released by fruit
to skillet after about 4 minutes. Off heat, whisk in butter and vanilla;
pour caramel mixture into prepared cake pan. Set aside while preparing
cake. (Pineapple will continue to release liquid as it sits; do not add
this liquid to already-reduced juice mixture.)
For the cake: Adjust oven rack to lower-middle position and heat
oven to 350 degrees. Whisk flour, baking powder, and salt in medium
bowl; set aside.
In bowl of standing mixer fitted with flat beater, cream butter and
sugar at medium-high speed until light and fluffy, 3 to 4 minutes.
Reduce speed to medium, add vanilla, and beat to combine; one at a time,
add whole eggs then egg white, beating well and scraping down bowl
after each addition. Reduce speed to low; add about one-third of flour
mixture and beat until incorporated. Add half of milk and beat until
incorporated; repeat, adding half of remaining flour mixture and
remaining milk, and finish with remaining flour. Give final stir with
rubber spatula, scraping bottom and sides of bowl to ensure that batter
is combined. Batter will be thick.
To bake: Working quickly, distribute cooked pineapple in cake pan
in even layer, gently pressing fruit into caramel. Using rubber
spatula, drop mounds of batter over fruit, then spread batter over fruit
and to sides of pan. Tap pan lightly against work surface to release
any air bubbles. Bake until cake is golden brown and toothpick inserted
into center of cake 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; lift off cake pan. Cool to room
temperature, about 2 hours; then cut into pieces and serve.