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Greek Orange Cake (Portokalopita)

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Greek Orange Cake (Portokalopita)
Chopped Phyllo dough gives this orange-scented custard cake from Crete its layered texture. This recipe will use about 6 large fresh oranges. Man, is it Good!
Ingredients
  1. 3 (1/8 inch thick) orange slices
  2. 1 2/3 cups fresh orange juice
  3. 1 1/2 cups sugar
  4. 1 (2 inch) stick cinnamon
  5. 14 Tablespoons extra-virgin olive oil, plus more for greasing pan
  6. flour for dusting pan
  7. 4 eggs
  8. 3/4 cup Greek yogurt
  9. 1/4 cup orange zest
  10. 1/2 tsp. vanilla extract
  11. 1/4 cup fine semolina
  12. 1 1/2 teaspoon baking powder
  13. 12 oz. country-style phyllo sheets, cut in 1/2 inch pieces
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Instructions
  1. Preheat oven to 325° F.
  2. Put orange slices in bottom of an 8" x 8" baking dish; pour 1 cup orange juice over top.
  3. Cover the baking dish with foil and bake until oranges are very soft, 40–45 minutes then transfer to a rack to cool.
  4. Meanwhile, bring ¾ cup sugar, cinnamon, and 1 ½ cups water to a boil in a 2-qt. saucepan to create the syrup. Cook for 5 minutes; remove from heat. Pour syrup over orange slices. Let cool completely.
  5. Grease a 9" x 13" baking dish and dust with flour; set aside.
  6. Combine remaining sugar and eggs in a bowl; beat with a hand mixer until pale and thick.
  7. Whisk in remaining orange juice, oil, yogurt, zest, and vanilla.
  8. In a separate bowl, whisk together semolina and baking powder then whisk into the egg mixture and stir in phyllo pieces.
  9. Pour mixture into prepared dish and bake until lightly browned, 35–40 minutes.
  10. Pour syrup evenly over cake; let cool.
  11. Cut cake into 12 squares and cut orange slices into quarters.
  12. Top each cake square with an orange quarter.
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