118459-90-8Relevant articles and documents
A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis
Pearson, Anthony J.,Lee, Kieseung
, p. 2304 - 2313 (2007/10/02)
Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13.An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic.Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.
The total synthesis of the isodityrosine-derived cyclic tripeptides OF4949-III and K-13. Determination of the absolute configuration of K-13
Evans,Ellman
, p. 1063 - 1072 (2007/10/02)
The asymmetric syntheses of the two cyclic tripeptides OF4949-III and K-13 have been completed. The absolute stereochemical assignment of the former compound has been confirmed, while the absolute configuration of the latter has been established for the f