Step 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.
Step 2: Meanwhile, bring the 3/4 cup sugar, cinnamon, and 1 1/2 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.
Step 3: Grease a 9" x 13" baking pan and dust with flour; set aside.
Step 4: Combine the other 3/4 cup 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.
Step 5: Pour mixture into prepared baking pan; bake until lightly browned, about 35–40 minutes. Test by inserting tip of sharp knife into cake; if it comes out clean, it's done.
Step 6: Pour the cold syrup evenly over cake; let cool. To serve, cut cake into 12 squares and cut orange slices into quarters; top each square with an orange quarter.
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