Synthesis of Vaniprevir (MK-7009): Lactamization To Prepare a 22-Membered Macrocycle
The Journal of Organic Chemistry2011Vol. 76(19), pp. 7804–7815
Citations Over TimeTop 10% of 2011 papers
Zhiguo J. Song, David M. Tellers, Michel Journet, Jeffrey T. Kuethe, David Lieberman, Guy R. Humphrey, Fei Zhang, Zhihui Peng, Marjorie S. Waters, Daniel Zewge, Andrew Nolting, Dalian Zhao, Robert A. Reamer, Peter G. Dormer, Kevin M. Belyk, Ian W. Davies, Paul N. Devine, David M. Tschaen
Abstract
Development of a practical synthesis of MK-7009, a 20-membered [corrected] macrocycle, is described. A variety of ring-closing strategies were evaluated, including ring-closing metathesis, intermolecular palladium-catalyzed cross-couplings, and macrolactamization. Ring closure via macrolactamization was found to give the highest yields under relatively high reaction concentrations. Optimization of the ring formation step and the synthesis of key intermediates en route to MK-7009 are reported.
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