Preheat oven to 350 degrees F (175 degrees C). Line two 8-inch round pans with parchment paper.
Sift 1 1/2 cups of the white sugar, flour, cocoa powder, baking soda, and salt together in a bowl. Beat shortening and remaining 1/2 cup white sugar together in a large bowl with an electric mixer until light and fluffy. Beat 1 egg at a time into the shortening mixture; add vanilla extract with last egg. Add portions of flour mixture alternately with buttermilk, beating after each addition to form a smooth batter. Pour batter into prepared baking pans.
Bake in preheated oven until a toothpick inserted into the center comes out clean, 35 to 40 minutes. Cool in the pans for 10 minutes before removing to cool completely on a wire rack.
Remove parchment from cake bottoms. Cut each layer in half horizontally, making 4 layers total. Pour 2 tablespoons cherry liqueur over each cake half.
Beat cream in a chilled glass or metal bowl with an electric mixer until stiff peaks form. Beat in 2 tablespoons cherry liqueur and 1/2 teaspoon vanilla extract. Beat in confectioners' sugar and salt until cream filling is smooth and stiff.
Spread 1 cake layer with 1/4 of the cream filling; top with 1/3 cherries. Repeat with 2 additional layers. Place 4th layer on top; frost top and sides of cake with remaining cream filling.
