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3/4 cup cocoa powder
125g unsalted butter, chopped
2 Tbsp extra virgin olive oil
1 cup caster sugar, plus 1 1/2 cups
1/2 cup brown sugar
2 tsp vanilla paste, plus 1 tsp extra
Cooking oil spray, to grease
2 free-range eggs
2 free-range egg yolks
1/2 cup Greek yoghurt
2 cups self-raising flour, sifted
500g frozen cherries
125ml cup brandy
200g white chocolate, chopped
250ml thickened cream, plus extra 200ml
3/4 cup icing sugar mixture
Preheat oven to 180°C fan forced (200°C conventional). Put cocoa powder, butter, olive oil, milk, caster sugar, brown sugar and vanilla in a medium saucepan over moderate heat. Bring to a simmer and cook for 2 minutes, remove from heat and set aside to cool completely.
Grease and line the base and side of a 22cm round cake tin with baking paper. Whisk eggs, yolks and yoghurt in a large bowl until smooth. Pour in cocoa mixture and whisk to combine. Fold in flour. Pour batter into prepared tin and bake for 50-55 minutes, until a skewer can be inserted and removed cleanly. Allow to cool in tin for 10 minutes before turning out, and cool completely on a wire rack.
Meanwhile, put extra sugar and 125ml water in a medium saucepan, stir to combine and place over medium heat. Cook without stirring for about 10 minutes, until a pale caramel forms; use a wet pastry brush to brush down sides of pan to prevent sugar crystals forming. Carefully add cherries and brandy and cook for a further 10 minutes. Pour out half the liquid and reserve. Simmer remainder until the liquid has thickened. Set both aside to cool.
Put chocolate and cream in a medium saucepan over low heat, stirring until melted. Set aside to cool to room temperature. Transfer to the bowl of an electric mixer and beat with whisk attachment until aerated. Add icing sugar, extra cream and vanilla and whip to soft peaks.
Using a large serrated knife, cut cake into 3 even layers. Drizzle each layer with reserved cherry syrup. Place one layer, cut side up, on a platter, top with 1/3 of the icing and 1/3 of the cherry mixture. Repeat with remaining layers.