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Orange Cake (Portokalopita)

From: Saveur

3 ⅛"-thick orange slices
1⅔ cups fresh orange juice
1½ cups sugar
1 2" stick cinnamon
14 tbsp. extra-virgin olive oil, plus more for greasing
flour, for pan
4 eggs
¾ cup Greek yogurt
¼ cup orange zest
½ tsp. vanilla extract
¼ cup fine semolina
1½ tsp. baking powder
12 oz. country-style phyllo sheets, cut in ½" pieces

1. Heat oven to 325°. Put orange slices in bottom of an 8" x 8" baking dish; pour 1 cup orange juice over top. Cover baking dish with foil. Bake until oranges are very soft, 40–45 minutes. Transfer to a rack to cool.

Use juice to make syrup....

2. Meanwhile, bring ¾ cup sugar, cinnamon, and 1½ cups water to a boil in a 2-qt. saucepan. Cook for 5 minutes; remove from heat. Pour syrup over orange slices. Let cool completely.

3. Grease a 9" x 13" baking dish and dust with flour; set aside. Combine remaining sugar and eggs in a bowl; beat with a hand mixer until pale and thick. Whisk in remaining orange juice, oil, yogurt, zest, and vanilla. In a separate bowl, whisk together semolina and baking powder, whisk into egg mixture, then stir in phyllo. Pour mixture into prepared dish; bake until lightly browned, 35–40 minutes. Pour syrup evenly over cake; let cool. Cut cake into 12 squares and cut orange slices into quarters; top each square with an orange quarter.