Preheat oven to 350 degrees. Coat a 13x9x2 pan with cooking spray.
Beat cake mix, oil, yogurt, and eggs on low for 30 seconds, then medium-high for 2 minutes. Spoon into pan and bake for 350 degrees for 35 minutes. Cool on rack for 15 minutes. Remove from pan and cool on rack. Trim off 1 inch edge, save for snacks. Cut cake into 1 inch cubes.
Beat heavy cream and rum extract until stiff peaks form. Gently fold in marshmallow cream, fold in crushed pineapple with its juices.
Place 1/2 cake cubes in 14-16 oz trifle dishes. Gently press to compact. Sprinkle 1/2 coconut and scatter in 1/2 cherries. Spoon 1/2 whipped cream, mix over cubes. Repeat layering. Cover and refrigerate for 3 hours. Garnish with toasted coconut.
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