Brush pineapple with a few tablespoons of oil and season with salt and pepper. Grill until golden brown on all sides. Remove pineapple from the grill, coarsely chop and transfer to the bowl of a food processor. Add the jalapeno, vinegar, coconut milk, cilantro, and few tablespoons of oil and honey, to taste. Season with salt and pepper. Let sit at room temperature for at least 30 minutes before serving.
For Rum-Molasses Glaze:
Heat 2 tablespoons of the oil in a medium saucepan over high heat. Add the onions and cook until soft. Add the garlic and cook for 30 seconds. Add the rum and cook until reduced by half. Add the stock, molasses, sugar, habanero, cinnamon sticks, and star anise. Bring to a boil, then lower the heat and cook until reduced by half, stirring occasionally, about 30 minutes.
Strain the mixture into a bowl then return it to the saucepan and continue cooking until reduced by half and thickened to a glaze. Season with salt and pepper. Pour the mixture into a bowl and let cool to room temperature.
Heat grill to high.
Brush the tenderloin with 2 tablespoons of oil and season with salt and pepper. Grill until crusty and charred on both sides and the internal temperature reaches 145 degrees F on an instant-read thermometer, brushing with the glaze during the last few minutes of grilling. Remove from the grill to a cutting board and brush with more of the glaze. Let rest 5 minutes before cutting into 1/2-inch thick slices. Spoon some of the sauce onto each plate, top with a few slices of pork, and drizzle with a little more of the sauce. Garnish with green onions and cilantro leaves.