In conclusion, we have successfully accessed a functionalized OBD as an AB-ring precursor for NOG and analogues through a highly regioselective benzyne cycloaddition strategy to give an oxa-benzonorbornadiene (OBD) A-ring fused to a functionalized aromatic B-ring. A new variation on a SmI2-mediated ring-opening gave regioselective ring-opening of the OBD to furnish a precursor for the A ring of NOG. More importantly, our studies on reductive ring-opening of the OBD led to several other platforms that could be readily elaborated to novel NOG analogues for SAR studies. Ongoing studies are implementing our proposed convergent three-fragment strategy to couple the AB-ring to the D-ring via XEC and a carbonylative intramolecular Friedel-Crafts reaction. Latestage glycosylations of both the A-and D-ring sugars will be followed by biocatalysis with SnoK to close the E-ring and afford NOG. More excitingly, demonstration of this modular synthetic strategy will afford a great degree of flexibility to probe the interplay of the appended sugars or aminosugars on analog activity.