RCM of tripeptide dienes containing a chiral vinylcyclopropane moiety: impact of different Ru-based catalysts on the stereochemical integrity of the macrocyclic products |
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Authors: | Poirier Martin Aubry Norman Boucher Colette Ferland Jean-Marie LaPlante Steve Tsantrizos Youla S |
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Institution: | Department of Chemistry, Boehringer Ingelheim (Canada) Ltd., Research and Development, 2100 Cunard Street, Laval, Quebec H7S 2G5, Canada. |
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Abstract: | structures: see text] Tripeptide dienes containing an (1R,2S)-vinyl aminocyclopropylcarboxylate residue were cyclized to beta-strand scaffolds under ring-closing metathesis (RCM). Conformational factors, ligand effects, and reaction conditions were evaluated. A protocol was developed for the efficient synthesis of 15-membered ring peptides in high diastereomeric purity. These peptides are key synthetic precursors to antiviral agents that target the hepatitis C virus and represent the first class of clinically validated pharmaceutical agents that are synthesized in large scale using RCM. |
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