Natural product and natural product-like molecules that contain a macrocycle are attractive synthetic targets because they contain novel molecular architectures and they are often biologically active. Previous efforts from our group delivered carbohydrate-fused and cyclohexane diol-fused [13] macro-dilactones. These macrodilactones featured a ring fusion that contained no atoms between the bridgehead carbons. Here we report on studies investigating macrocyles that are fused at the C1 and C6 positions of a pyranose ring. The 1,6 connectivity to the carbohydrate affords a one atom bridge in the bicyclic system. Concurrently, the introduction of an amide to the macrocycle to yields a carbohydrate fused macrolactam. The new macrolactams have been produced via a concise synthetic sequence that includes acylation of a 6-amino galactose followed by glycoslyation and ring closing metathesis (RCM). Structural investigation of the new macrolactams will be followed by an assay of their biological activity.