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For the pineapple: Mix together the rum, brown sugar and vanilla extract in a medium bowl. Add the pineapple and toss until well coated. Cover and refrigerate for at least 1 hour.
For the coconut garnish: In a dry saute pan over medium-low heat, toast the coconut flakes until light golden, 4 to 5 minutes. Set aside.
Set a saute pan over medium heat. Add the butter and marinated pineapple, bring to a simmer and simmer until thickened, about 10 minutes.
For the whipped cream: Just before serving, whip the cream, powdered sugar and vanilla extract until lightly thickened.
Divide the pineapple between 2 bowls, spooning over the extra sauce. Top each bowl with half of the ice cream, whipped cream and toasted coconut.
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