Preheat oven to 325 degrees F.

Make caramel. Add ⅔ cup (133 grams) sugar in a saucepan and melt over medium heat. Reduce heat to low and continue to cook until sugar is an amber brown caramel. Stir occasionally during simmering to avoid burning. Pour caramel into a loaf pan and set aside for 10 minutes.

Prepare flan mixture. Combine pumpkin puree, evaporated milk, condensed milk, eggs, vanilla, cinnamon, salt, nutmeg, ginger, and allspice. Whisk until well combined. Transfer mixture into a measuring cup with a spout.

Make chocolate cake batter. Combine flour, sugar, cocoa powder, salt, and baking powder in a large bowl.

In a separate bowl, whisk together milk, olive oil, egg white, and vanilla. Add wet ingredients to dry ingredients, mixing until combined.

Pour chocolate cake batter over caramel in loaf pan, spreading it an even layer. Place a spatula over the chocolate cake and carefully pour the flan mixture over the spatula into the loaf pan. This will prevent holes in the cake.

Place the loaf pan in a 9x13 inch baking dish. Add enough boiling water in the baking dish to come up halfway up the sides of the loaf pan. Bake pumpkin chocoflan for 45-55 minutes or until the internal temperature registers 180 degrees F. Remove from oven and let cool for 15 minutes. Transfer to the fridge and chill uncovered at least 8 hours or overnight.

When ready to serve, dip the bottom of the loaf pan into a skillet filled with hot water. The water will help loosen the caramel on the bottom. Run an offset spatula around the edges of the pan to loosen the can. Carefully place a platter on top of the loaf pan and invert the cake. Serve at room temperature or cold.