For the cake: Preheat the oven to 400 degrees F. In a small bowl, combine the 2 teaspoons flour and 1/2 teaspoon sugar. Brush an 8-inch round cake pan with olive oil and then dust with the flour-sugar mix.
With a stand mixer fitted with the whisk attachment, beat the eggs on high speed with the 1 1/3 cup sugar until they turn opaque, 3 to 4 minutes. Switch to the paddle attachment and add the milk, the 1/2 cup olive oil, the cream and orange zest. Mix the 1 1/3 cup flour, the yeast and salt together and incorporate into the batter, scraping down the sides as needed. Combine well, 2 to 3 minutes. Allow the batter to rest in a warm place 10 to 15 minutes.
Pour the batter into the prepared cake pan and bake until toothpick inserted comes out clean, 30 to 35 minutes. Remove from oven allow to cool in the pan 10 minutes. Run a small knife around the edge of the pan, turn the pan over, tapping if necessary to release the cake, and place on a rack and allow to cool completely. Once cool, invert and place on a rimmed cake plate.
For the syrup: Remove the zest from the orange using a peeler, avoiding the pith, and place in a medium saucepan with the orange juice and sugar. Cook over medium heat until a thick syrup forms, 45 minutes to 1 hour.
Strain and discard the zest strips. Pour 1/2 the syrup over the cooled cake, and then pierce the surface with a fork to allow the syrup to soak into the cake. Return the remaining syrup to the stove and continue to reduce until very thick and syrupy, an additional 15 to 20 minutes.
For the toppings: In a small skillet, lightly toast the pine nuts over medium heat until just starting to color, 3 to 4 minutes. Roughly chop the pine nuts.
Arrange the segmented oranges around the outside edge of the cake and place a small fan of them in the center. Garnish with the pine nuts and drizzle with the reduced syrup. Cut into slices and serve with creme fraiche.