In this presentation the parallel synthesis of several novel amide, sulfonamide, and urea libraries from unsaturated eight-membered lactam scaffolds is described. These heretofore unknown scaffolds were prepared by the efficient ring-closing metathesis of the corresponding diene amides. The compound libraries were inspired by the rare class of complex, saturated eight-membered lactone natural products. This class includes the antitumor octalactins, cephalosporolide D, dregeanin, and the putative structures of the gonioheptolides.