Application of ring-closing metathesis for the synthesis of macrocyclic peptidomimetics as inhibitors of HCV NS3 protease |
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Authors: | Velázquez Francisco Venkatraman Srikanth Wu Wanli Blackman Melissa Prongay Andrew Girijavallabhan Viyyoor Shih Neng-Yang Njoroge F George |
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Affiliation: | Schering-Plough Research Institute, 2015 Galloping Hill Road, K-15-3 3545, Kenilworth, New Jersey 07033-1300, USA. francisco.velazquez@spcorp.com |
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Abstract: | An efficient synthetic approach for the preparation of macrocyclic peptidomimetics for inhibition of HCV NS3 is presented. The macrocyclic core is built using ring-closing metathesis (RCM) of a tripeptidic diene. The presented approach allows the introduction of heteroatoms in strategic places along the macrocyclic ring. The methyl ester moiety in the RCM products was synthetically manipulated to install a keto-amide moiety via a Passerini reaction. |
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