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. 2011 Oct 7;76(19):7804-15.
doi: 10.1021/jo2011494. Epub 2011 Aug 31.

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

Affiliations

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

Zhiguo J Song et al. J Org Chem. .

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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