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1
Bring the raisins and vin santo to a simmer in a very small saucepan over high heat. Turn off the heat and set aside for the raisins to absorb the wine for at least 30 minutes or up to overnight.
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2
Adjust an oven rack to the middle position and preheat the oven to 325u00b0F.
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3
Spread the pine nuts on a baking sheet and toast them in the oven for 8 to 10 minutes, until they are fragrant and golden brown, shaking the baking sheet and rotating it from front to back halfway through the cooking time so the nuts brown evenly. Remove the pine nuts from the oven and set them aside to cool to room temperature.
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4
Increase the oven temperature to 400u00b0F. Spray a 10-inch angel food pan generously with nonstick cooking spray and dust it lightly with flour.
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5
Leaving the peels attached, lay the orange halves flat side down and cut into 1/4-inch-thick slices. Chop the slices into 1/4-inch-thick cubes.
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6
Put the eggs, Italian leavening, and 1/2 cup plus 2 tablespoons of the granulated sugar in the bowl of a standing mixer fitted with the whisk attachment and mix on medium-high speed until the mixture thickens, 3 to 4 minutes. Gradually add the olive oil by pouring it down the side of the bowl in a slow, steady stream and mix until the batter is emulsified. Reduce the mixer speed to low. Add one-third of the flour and mix until it is no longer visible. Add one-third of the raisins and mix just to incorporate them. Stop the mixer and scrape down the sides of the bowl. Repeat two more times, mixing in one-third of the flour at a time, then one-third of the raisins at a time, and stopping to scrape down the sides of the bowl between additions, until all of the flour and all of the raisins have been incorporated.
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7
Turn off the mixer and remove the bowl from the stand. Add the chopped oranges and use a rubber spatula to gently fold them into the batter. Set the batter aside to rest for 10 minutes. Scrape the batter into the prepared pan and scatter the pine nuts over the top. Sprinkle the cake with the remaining 1/4 cup granulated sugar and stick the tufts of rosemary into the batter, distributing them over the surface of the cake in an attractive way.
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8
Bake the cake for 10 minutes. Rotate the cake and lower the oven temperature to 325u00b0F. Bake the cake for another 30 to 35 minutes, until the cake is golden brown and a toothpick inserted comes out clean, rotating the cake once during the baking time so it browns evenly. Remove the cake from the oven and set it aside to cool to room temperature.
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9
To serve, run a knife or offset spatula around the inside of the pan to release the cake from the pan and put a large plate over the top of the pan. Swiftly flip the cake and the plate to invert the cake onto the plate. Invert the cake again onto a large serving plate or cake stand. Pour the confectioners' sugar into a fine-mesh strainer and tap the strainer over the cake to dust the cake lightly with the sugar. Serve the cake with a cake spatula or knife for guests to cut the size serving they want and serve themselves.
