Synthesis of vaniprevir (MK-7009): lactamization to prepare a 20-membered [corrected] macrocycle
- PMID: 21838271
- DOI: 10.1021/jo2011494
Synthesis of vaniprevir (MK-7009): lactamization to prepare a 20-membered [corrected] macrocycle
Erratum in
- J Org Chem. 2011 Nov 18;76(22):9553
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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