Anodic amide oxidation/olefin metathesis strategies: Developing a unified approach to the synthesis of bicyclic lactam peptidomimetics

Laura M. Beal, Bin Liu, Wenhua Chu, Kevin D. Moeller

Research output: Contribution to journalArticlepeer-review

73 Scopus citations

Abstract

In connection with efforts to build constrained peptidomimetics for the endocrine hormone TRH, a general strategy for the construction of bicyclic lactam peptide building blocks has been developed. This strategy used an anodic amide oxidation to selectively functionalize proline and then an olefin metathesis to build the desired lactam constraint. The route described provides a single approach for synthesizing both fully functionalized TRH analogs having seven- and eight-membered ring lactam constraints, as well as six- and seven-membered ring lactam analogs without the sidechain on the central amino acid.

Original languageEnglish
Pages (from-to)10113-10125
Number of pages13
JournalTetrahedron
Volume56
Issue number52
DOIs
StatePublished - Dec 22 2000

Keywords

  • Anodic amide oxidation
  • Bicyclic lactum peptidomimetics
  • TRH-R

Fingerprint

Dive into the research topics of 'Anodic amide oxidation/olefin metathesis strategies: Developing a unified approach to the synthesis of bicyclic lactam peptidomimetics'. Together they form a unique fingerprint.

Cite this