Synthesis of Vaniprevir (MK-7009): Lactamization To Prepare a 22-Membered Macrocycle

Autor:	Ian W. Davies, Paul N. Devine, Robert A. Reamer, David M. Tschaen, Fei Zhang, Daniel Zewge, Jeffrey T. Kuethe, David R. Lieberman, Zhihui Peng, Kevin M. Belyk, David M. Tellers, Guy R. Humphrey, Peter G. Dormer, Michel Journet, Andrew Nolting, Marjorie S. Waters, Dalian Zhao, Zhiguo J. Song
Rok vydání:	2011
Předmět:	chemistry.chemical_compound Stereochemistry Chemistry Vaniprevir Organic Chemistry Ring (chemistry) Metathesis
Zdroj:	The Journal of Organic Chemistry. 76:7804-7815
ISSN:	1520-6904 0022-3263
Popis:	Development of a practical synthesis of MK-7009, a 22-membered 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
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d1dc6683cb1f9b4cbaa077ffc9b2d32f https://doi.org/10.1021/jo2011494 Zobrazit plný text záznamu