Mom often made pineapple upside-down cake, the most famous of Haitian desserts, augmenting a boxed mix with various spices and extracts brought from Haiti by visiting relatives and popping a can of pineapple (and some freakishly red maraschino cherries) for the topping.
Mom was busy with a demanding job and two kids. I have a little more time on my hands, so I look to fresh pineapple, caramelizing it with maple syrup and spices then tiling it onto the bottom of the pan before baking the cake. Believe me, it’s worth the effort. When you haul the cake from the oven, the heady perfume of vanilla, almond, cinnamon, and star anise fills the room. When you flip the cake and lift the pan, the pineapple slices glisten like jewels and stun your friends waiting at the table.
Haitian Spiced Pineapple Upside-Down Cake
For the pineapple topping
- 3/4 cup virgin coconut oil plus more for greasing the pan
- 1 ripe pineapple
- 1/2 cup coconut sugar
- 1/2 cup maple sugar
- Three 3-inch cinnamon sticks
- 5 star anise
For the cake
- 2 3/4 cups Paleo-Friendly Flour Blend
- 1 tablespoon plus 1 teaspoon baking powder
- 1 teaspoon kosher salt
- One 1-inch piece cinnamon stick
- 2 cups coconut sugar
- 3/4 cup melted virgin coconut oil
- 5 large eggs
- 1/2 cup well-shaken coconut milk
- 2 tablespoons vanilla extract
- 2 teaspoons almond extract
- 1 lime, for zesting
Make the topping
- Trace the outside of an 11-inch pan onto a piece of parchment paper to make a rough circle about 1 inch bigger than the pan, then cut out the circle. You want the parchment to be just a tad bigger than the base of the pan so it has a little lip to contain the topping. Tuck the parchment into the base of the pan and rub it and the sides of the pan with a little coconut oil.
- Carve off the brown eyes, quarter the pineapple, and cut off and discard the core. Cut the quarters crosswise into 1/8-inch-thick slices.
- Set a mesh strainer over a large heatproof bowl. Combine the remaining coconut oil, coconut sugar, maple syrup, cinnamon sticks, and star anise in a large saucepan and bring to a simmer over medium heat.
- Add the pineapple and simmer until it releases its juices and they reduce into a rich syrup and the pineapple is very golden, translucent, and tender, about 10 minutes. Pour the mixture through the strainer. Reserve the pineapple, discard the whole spices, and pour the strained liquid back into the saucepan. Continue reducing the liquid until it’s as thick as molasses, about 8 minutes more. Set the liquid aside.
- Starting from the dead center of the parchment, lay down once piece of pineapple, then shingle the remaining pineapple slices into a spiral, overlapping each slice over the last in an outward circular pattern, until you cover the entire base of the pan. Set aside while you prep the cake batter.
Make the cake
- Preheat the oven to 350°F and move an oven rack to the center position. In a medium mixing bowl, combine the flour blend, baking powder, and salt and stir well. Use a Microplane to grate in the cinnamon. In a large mixing bowl, whisk together the coconut sugar and coconut oil until combined. Whisk in the eggs one at a time, fully incorporating each one before adding the next. Whisk in the coconut milk, vanilla extract, and almond extract until the mixture is well combined, thick, and creamy. As you lift the whisk from the bowl, the mixture should slowly and steadily fall back into the bowl. Use a Microplane to grate in the lime zest. Working in two batches, add the flour to the bowl with the wet ingredients and fold it in, completely incorporating the first batch before adding the second.
- Pour the reserved caramelized sauce evenly over the shingled pineapple. Next, pour the cake batter evenly over the sauce. Bake the cake on the center rack until golden brown and a thermometer reads 200°F when inserted in the center (temperature is the best way to tell when cakes made with my Paleo-friendly flour blend are ready), about 35 minutes.
- When the cake is done, run a knife around the edges to make sure it releases from the pan. Grab a plate or lightweight cutting board that’s slightly larger than the pan and invert the plate onto the pan. Protecting your hands from the hot pan with oven mitts or a kitchen towel, firmly grab the sides of both the pan and the plate and swiftly invert the pan onto the plate. Let the plate rest on the counter for a few seconds, then carefully remove the pan, slowly lifting from one side, then the other, to expose the cake.
- If any pineapple pieces have stuck to the pan, use a small spatula to gently dislodge them and use them to cover any of the cake’s bald spots.
- Let the cake rest for at least 15 minutes before serving. Leftovers keep in an airtight container at room temperature for up to 4 days.