Development of New Stereodiverse Diaminocyclitols as Inhibitors of Influenza Virus Neuraminidase

A concise and modular approach to synthesize a new type of cyclopentene-based diaminocyclitol library from d-serine and l-serine has been developed, and key steps in this synthesis are an aza-Claisen rearrangement, a ring-closing metathesis, and a Baylis−Hillman reaction. The developed chemistry may offer a unique way to investigate the neuraminidase (NA) mutation by systematically mapping the changes within its binding sites.