Add all the ingredients except the club soda to a shaker and fill with ice. Shake, and fine-strain into a rocks glass filled with fresh ice. Top with a splash of club soda and garnish with a lemon wheel.
*Caramelized Pineapple Syrup
Melt the butter in a large, heavy-bottomed saucepan over medium heat. Add the pineapple slices and cook, turning occasionally, until darkly caramelized (10 to 15 minutes). Deglaze the pan with the rum. Add the sugar and stir vigorously until it melts into a bubbling mass. Slowly add the pineapple juice and stir to incorporate. Remove from the heat and let cool. Strain, puree the fruit and stir back into the liquid.
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