1. Combine granulated sugar, 3 tablespoons bourbon, 3 tablespoons water, and juice in a medium saucepan over medium-high heat; cook 2 minutes or until sugar dissolves, stirring constantly. Bring to a boil; reduce heat to medium and cook, without stirring, 10 minutes or until golden. Remove from heat. Carefully add cream, stirring constantly (mixture will bubble vigorously). Cool slightly. Stir in remaining 2 teaspoons bourbon and vanilla.
2. Preheat broiler to high.
3. Cut pineapple lengthwise into 12 slices; cut each slice in half crosswise. Arrange pineapple on a foil-lined broiler pan coated with cooking spray; sprinkle evenly with brown sugar. Broil 5 inches from heat for 12 minutes or until golden brown.
4. Scoop 1/3 cup ice cream into each of 6 bowls. Arrange 4 pineapple slices in each bowl; top each serving with 2 1/2 tablespoons caramel sauce. Sprinkle each serving with 2 teaspoons coconut; serve immediately.