cis-Aziridine Synthon Based Synthetic Investigation for Tamiflu Employing Horner-Wadsworth-Emmons Reaction

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.

Automated summary

The study presents a synthetic approach to achieve a novel intermediate of Tamiflu using cis-aziridine as a chiral building block and (D)-mannitol as a renewable starting material. The intramolecular Horner-Wadsworth-Emmons reaction is utilized as the key step for Tamiflu synthesis. However, the diene containing allylic aziridine framework is found to be inefficient in providing the core skeleton of Tamiflu through ring-closing metathesis reaction.