Preheat oven to 350 degrees F. Coat bottom and sides of a 9" round cake pan with cooking spray.
In a small saucepan, melt the 2 tablespoons butter over low heat; stir in the brown sugar. Spread mixture in bottom of pan. Arrange pineapple slices on top of brown sugar mixture, with a maraschino cherry in the middle of each. Set aside.
Measure the flour blend by lightly spooning into measuring cup and leveling off with the back of a knife. Whisk together the flour blend, baking powder and salt in a medium bowl.
In large mixing bowl, beat the 6 tablespoons softened butter and granulated sugar on medium speed until light and fluffy, about 2 minutes. Beat in the eggs, milk, and vanilla until smooth. Slowly add the flour mixture while mixing on low speed. Blend until batter is smooth.
Carefully spread batter over pineapple slices in prepared cake pan. Bake 55 to 60 minutes, or until toothpick inserted near center comes out clean.
Immediately from the oven, run a knife around the edge of cake to loosen from the pan sides. Invert onto serving plate.
Cool completely and serve with whipped cream, if desired.
Notes
This recipe does have quite a bit of sugar, so use your judgement for how large of a piece you will be able to tolerate.