147240-35-5Relevant academic research and scientific papers
A second-generation synthesis of scalemic 3,5,5-trisubstituted pyrrolin-4-ones: Incorporation of functionalized amino acid side-chains
Smith III, Amos B.,Benowitz, Andrew B.,Favor, David A.,Sprengeler, Paul A.,Hirschmann, Ralph
, p. 3809 - 3812 (2007/10/03)
To access mimics of peptide β-strands (1), scalemic 3,5,5-trisubstituted pyrrolin-4-ones bearing the tyrosine, serine, and lysine side-chains have been generated via cyclization of metalated imino esters and deprotection. The functionalized imino esters were prepared by asymmetric alkylation of a common oxazolidinone precursor (2) derived from L-rhenylglycine.
De novo design, synthesis, and X-ray crystal structures of pyrrolinone-based β-strand peptidomimetics
Smith III, Amos B.,Guzman, Mark C.,Sprengeler, Paul A.,Keenan, Terence P.,Holcomb, Ryan C.,Wood, John L.,Carroll, Patrick J.,Hirschmann, Ralph
, p. 9947 - 9962 (2007/10/02)
The de novo design and synthesis of a novel non-peptide scaffolding for β-strand/sheet mimics are described. The scaffold consists of repeating 3,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains. The iter
AN EFFECTIVE SYNTHESIS OF SCALEMIC 3,5,5-TRISUSBSTITUTED PYRROLIN-4-ONES
Smith, Amos B.,Holcomb, Ryan C.,Guzman, Mark C.,Keenan, Terence P.,Sprengeler, Paul A.,Hirschmann, Ralph
, p. 63 - 66 (2007/10/02)
A new two-step method employs the intramolecular cyclization of metalated imino esters for the construction of scalemic 3,5,5-trisubstituted pyrrolin-4-ones (4).The imino esters in turn derive from α-disubstituted amino acids, the latter readily available
