1 medium pineapple, peeled, cored, and quartered lengthwise
2 tablespoons dark brown sugar
1 cinnamon stick
1 star anise pod
2 whole cloves
1 vanilla bean, split lengthwise, seeds scraped and reserved
1/3 cup dark rum
Heat oven to 350°F. Melt butter in a large frying pan over medium heat. When it begins to foam, add pineapple quarters cut side down and cook until nicely browned. Flip and repeat until second side is well browned.
Remove the pan from heat and add brown sugar, cinnamon, star anise, cloves, vanilla seeds and pod, and about 1/2 of the rum. Place the pan in the oven and roast for 5 minutes. Turn over pineapple pieces and roast until pineapple is soft and caramelized, about 5 minutes more.
Remove the pan from the oven, add remaining rum, and scrape to incorporate any of the browned bits into the liquid. Allow to cool, then remove pineapple and slice for serving. Remove spices and reserve remaining sauce for drizzling.