Pineapple upside down cake

Makes 1 large cake (60mm diameter x 240 mm width x 290mm length)


  • Pineapple sugar syrup
    • 1 super sweet pineapple
    • 500 ml litre water
    • 200g caster sugar
    • 2 vanilla pods split lengthways and seeds split out
    • 1 cinnamon stick
    • 2 star anise
    • 2 bay leaves
  • Topping
    • 150g soft butter
    • 150g soft dark brown sugar
    • 3tsp cracked black pepper
    • 4tbsp chopped dates
    • 50ml dark rum
  • Cake Mix
    • 200g butter
    • 200g soft brown sugar
    • 100g self raising flour, sifted
    • 2 tsp baking powder
    • 2 vanilla pods, split and seeds scraped out
    • 4 whole eggs
    • 50ml dark rum (optional – this was left out on Vt for school kids!)
  • Extra toffee sauce to serve
    • 75g butter
    • 100g soft brown sugar
    • 30ml dark rum
    • Finely grated zest of a lime
  • Coconut cream
    • 2tbsp caster sugar
    • 2 x 160ml cans of coconut cream, chilled overnight
    • Zest of 1 lime


  1. Firstly, trim the outside of the pineapple and cut out all of the eyes. Cut the pineapple into rings of around 1cm-1.5cm – you will need to use 4 or five these slices for the cake. Use a small ring cutter to cut out the centre of each pineapple, and a large ring cutter to make each pineapple ring a uniform shape. Pour the water into a pan and add the caster sugar, vanilla pod, cinnamon stick, star anise and bay leaves. Bring the pan to the boil. Place the pineapple rings into the liquid and turn the temperature down to a low simmer. Cook for 15-20 minutes until the pineapple is just cooked. Turn the heat off and let the pineapples cool in their own liquid.
  2. Butter your cake tin
  3. With an electric whisk, beat together the soft butter and 50g of soft dark brown sugar until creamy. Add the chopped dates and the cracked black pepper to the butter and sugar mix.
  4. Drain the pineapple slices and place them into the cake tin.
  5. Spread the topping mix over the pineapple covering the bottom of the cake tin.
  6. With your electric whisk, beat together the of butter and the soft dark brown sugar until creamy. Add the sifted flour, baking powder, eggs, vanilla seeds and the dark rum if using. Spoon this cake mix into the tin and smooth it down so its level. Bake in a pre-heated oven at 180°C for 45 minutes. Remove from the oven and leave to stand for 10-15 minutes, then turn it out onto a plate, ready for serving.
  7. For the extra toffee sauce just melt everything together (sugar, rum, butter) in a pan, bring to the boil, then let cool.
  8. Coconut cream to serve
    1. Open the two cans of chilled coconut cream and place it into a mixing bowl with the 2tbsp of caster sugar. Whisk until light and fluffy and serve on the side with the cake, with the grated lime zest.