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Preheat oven to 350°F. Grease and flour 2 8" round pans and set aside.
Crush oranges with food processor or blender.
In a large bowl/mixer, cream butter and sugar until fluffy. Beat in egg yolks, crushed mandarin oranges and vanilla.
In a separate bowl, sift cake flour, baking powder and salt together.
Gradually incorporate into wet mixture, alternating with milk until just incorporated.
Pour into baking pans and bake 25-28 minutes when cake springs back after being touched. Allow to cool 20 minutes before turning onto rack or pedestal.
Crush fresh pineapple in food processor or blender. Set aside.
In a stand mixer, beat heavy whipping cream until stiff. Gradually add powdered sugar, crushed pineapple and optional vanilla pudding mix.
Place one layer of cake onto your serving dish and fill with icing before placing the second layer on top. Ice, garnish and refrigerate until ready to serve.