Synthetic investigations to achieve a novel intermediate of Tamiflu by using cis-aziridine as a chiral building block, which is readily synthesized from (D)-mannitol as a renewable starting material, has been presented. The present approach utilizes the intramolecular Horner-Wadsworth-Emmons reaction as the key step for the synthesis of Tamiflu. On the other hand, diene containing allylic aziridine framework is found to be inefficient to furnish the six-membered core skeleton of Tamiflu through ring-closing metathesis reaction.

Foreign