Synthesis of the HCV protease inhibitor Vaniprevir (MK-7009) using ring-closing metathesis strategy
| Autor: | Jacob M. Janey, Robert F. Dunn, Michael J. Zacuto, Cheng-yi Chen, Jongrock Kong, Jaume Balsells-Padros, Sarah J. Dolman, Hongmei Li, Yang Cao |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
Cyclopropanes
Sulfonamides Indoles Diene Molecular Structure Proline Stereochemistry Vaniprevir Lactams Macrocyclic Organic Chemistry Substrate (chemistry) Isoindoline Hepacivirus Isoindoles Metathesis Catalysis Ruthenium chemistry.chemical_compound Ring-closing metathesis chemistry Cyclization Leucine Yield (chemistry) Hcv protease Protease Inhibitors |
| Zdroj: | The Journal of organic chemistry. 77(8) |
| ISSN: | 1520-6904 |
| Popis: | A highly efficient synthesis of Vaniprevir (MK-7009) has been accomplished in nine linear steps and 55% overall yield. The key features of this synthesis include a cost-effective synthesis of the isoindoline subunit and efficient construction of the 20-membered macrocyclic core of Vaniprevir (MK-7009) utilizing ring-closing metathesis technology. A high-performing ring-closing metathesis protocol has been achieved by simultaneous slow addition of the ruthenium catalyst (0.2 mol %) and the diene substrate at a concentration of 0.13 M. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|