Synthesis of vaniprevir (MK-7009): lactamization to prepare a 20-membered [corrected] macrocycle

Autor: Zhiguo J, Song, David M, Tellers, Michel, Journet, Jeffrey T, Kuethe, David, Lieberman, Guy, 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
Rok vydání: 2011
Předmět:
Zdroj: The Journal of organic chemistry. 76(19)
ISSN: 1520-6904
Popis: 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.
Databáze: OpenAIRE