in 2 quart saucepan, cook pudding mix, milk and pineapple juice as directed on box.
in 9 inch spring form pan, place a single layer of cookies. top with a single layer of pineapple. pour 2 cups of the cooked pudding on top. repeat layers, using remaining cookies, pineapple and pudding (you will be short 1 pineapple slice on top, add extra cookies to this spot). cover and refrigerate at least 8 hours or overnight.
in chilled medium bowl, beat whipping cream with electric mixer on medium speed until soft peaks form. add powdered sugar, beat until incorporated.
to serve, carefully remove side of spring form pan. top cake with whipped cream just before serving.