For the Pineapple Tarte Tatin, begin by making the rough puff pastry. Place flour and 125g of the unsalted butter into a medium bowl. Using your fingertips, gently press the butter into the flour leaving some lumps of butter visible.
Slowly pour in 50ml of cold water and bring the mixture together to form a slightly dry dough. Wrap the dough in plastic wrap and set aside in the fridge to rest for 30 minutes.
Lightly flour a clean work surface. Once rested, remove dough from the fridge, unwrap and roll out onto the floured surface into a 10cm x 30cm rectangle. Fold the shorter ends of the rectangle towards the middle to so that they overlap each other and create 3 layers. Turn the dough 90 degrees clockwise and roll out again to a 10cm x 30cm rectangle. Repeat the rolling and folding process 2 more times. Wrap in cling film and return the pastry to the fridge until needed.
Peel and slice the pineapple into slices approximately 5mm thick.
Place the remaining 15g of butter in a 20cm ovenproof non-stick frypan over medium heat until butter begins to foam. Add the pineapple slices and fry until golden brown and caramelised on one side. Turn pieces over and caramelise the other side. Remove from the heat and set pineapple pieces aside on a plate.
Wipe out the frypan used to cook the pineapple and sprinkle the caster sugar in an even layer into the frypan. Place pan over medium heat and cook until sugar melts and reaches a deep golden brown colour. Add the caramelised pineapple slices in one even layer and remove the pan from the heat.
Lightly flour a clean work surface. Remove the pastry from the fridge and place on the floured surface. Roll pastry out into a 20cm circle, approximately 5mm thick.
Lay the pastry neatly over the pineapple layer and along the edges of the frypan. Trim the excess pastry away with a sharp knife and tuck the edges into the frypan to cover caramelised pineapple.
Place the frypan into the oven to bake until the pastry is puffed and golden, about 12-15 minutes.
Remove pastry from oven and carefully invert onto a clean large serving plate. Set aside.
For the Pumpkin Chilli Caramel, place pumpkin into a slow juicer and juice. Transfer pumpkin juice to a small saucepan and reserve the pulp in a small bowl.
Add sliced red chilli to the saucepan of pumpkin juice. Place over medium heat and simmer until the liquid has reduced by half. Remove from heat and set aside, keeping warm.
Meanwhile, place sugar in a small saucepan and melt over a low heat until deep golden brown. Strain the reduced pumpkin juice into the caramel then whisk in the butter & cream until completely incorporated. Transfer to a serving jug and set aside until needed.
For the Toasted Pumpkin, line a baking tray with baking paper. Spread the reserved pumpkin pulp in an even layer onto the lined baking tray and place into the oven to roast until slightly dried, about 12-15 minutes. Remove from the oven, place pumpkin into a small bowl and stir through the sugar and butter. Return the pumpkin mixture to the lined baking tray and spread out. Place back into the oven to bake until the edges of the pumpkin begin to turn brown, about 10-15 minutes. Remove from the oven and set aside.
For the Pineapple Chilli Salsa, place all ingredients together in a bowl and toss to combine. Set aside.
To finish, spoon some of the Toasted Pumpkin onto the centre of the Pineapple Tarte Tatin. Top the Toasted Pumpkin with the Pineapple Chilli Salsa. Spoon some freshly whipped cream into a ramekin and top with some of the Toasted Pumpkin. Serve with the ramekin of whipped cream and jug of Pumpkin Chilli Caramel to the side.