RCM of Tripeptide Dienes Containing a Chiral Vinylcyclopropane Moiety: Impact of Different Ru-Based Catalysts on the Stereochemical Integrity of the Macrocyclic Products

Citations Over TimeTop 10% of 2005 papers

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.

Related Papers

• → MO Tripeptide Diastereomers (M =99/99mTc, Re): Models To Identify the Structure of99mTc Peptide Targeted Radiopharmaceuticals(2007)36 cited
• → Synthesis of Small Cyclic Peptides via Reverse Turn Induced Ring Closing Metathesis of Tripeptides(2002)25 cited
• → Synthesis of a cyclic pseudo 310 helical structure from a β-amino acid-l-proline derived tripeptide via a ring closing metathesis reaction(2002)23 cited
• → Studies on Separation of Amino Acids and Related Compounds. IV. Separation of Diastereomeric Tripeptides Containing Basic and Acidic Amino Acid Residue(1968)8 cited
• → Metathesis Reactions in Solid‐Phase Organic Synthesis(2010)2 cited