Synthesis of the HCV Protease Inhibitor Vaniprevir (MK-7009) Using Ring-Closing Metathesis Strategy
The Journal of Organic Chemistry2012Vol. 77(8), pp. 3820–3828
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Jongrock Kong, Cheng‐yi Chen, Jaume Balsells-Padros, Yang Cao, Robert F. Dunn, Sarah J. Dolman, Jacob M. Janey, Hongmei Li, Michael J. Zacuto
Abstract
A highly efficient synthesis of Vaniprevir (MK-7009) has been accomplished in nine linear steps and 55% overall yield. The key features of this synthesis include a cost-effective synthesis of the isoindoline subunit and efficient construction of the 20-membered macrocyclic core of Vaniprevir (MK-7009) utilizing ring-closing metathesis technology. A high-performing ring-closing metathesis protocol has been achieved by simultaneous slow addition of the ruthenium catalyst (0.2 mol %) and the diene substrate at a concentration of 0.13 M.
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