In a large bowl, dissolve yeast in warm water. Add 1 tablespoon sugar; let stand for 5 minutes. Add milk, 1/4 cup butter, eggs, salt, remaining sugar and 1-1/2 cups flour. Beat until smooth. Stir in enough remaining flour to form a soft dough.
Turn onto a floured surface; knead until smooth and elastic, about 6-8 minutes. Place in a greased bowl, turning once to grease top. Cover and let rise in a warm place until doubled, about 45 minutes.
Punch dough down. Turn onto a floured surface; divide in half. Roll each into a 12x8-in. rectangle. Brush with some of the remaining butter. Roll up, jelly-roll style, starting with a long side. Pinch seam to seal.
Cut each into 12 slices. Place, cut side down, 2 in. apart on greased baking sheets. Brush with remaining butter. Cover and let rise in a warm place until doubled, about 30 minutes. Preheat oven to 425°.
Meanwhile, in a small saucepan, combine cornstarch and pineapple until blended. Bring to a boil over medium heat; cook and stir for 2 minutes or until thickened. Remove from the heat.
Place a teaspoonful of filling in the center of each roll. Bake until golden brown, 12-16 minutes. Remove from pans to wire racks.
For glaze, combine sugar, vanilla and enough milk to achieve desired consistency. Drizzle over warm rolls.