Cook penne by directions and drain. Meanwhile combine undrained tomatoes, tomato paste, wine/juice, sugar, oregano and pepper. Blend until smooth. In large skillet brown beef. Drain fat. Stir in tomato mix and boil. Reduce heat and simmer for 10 minutes. Stir in pasta and olives. Divide into 6 individual casseroles. Bake, covered, in 375 degree oven for 15 minutes or pour all mix into 2 quart casserole and bake 30 minutes. Sprinkle with chese and bake another 5 minutes.