Anodic Amide Oxidation/Olefin Metathesis Strategies: Developing a Unified Approach to the Synthesis of Bicyclic Lactam Peptidomimetics |
| |
Authors: | Laura M Beal Bin Liu Wenhua Chu Kevin D Moeller |
| |
Institution: | Department of Chemistry, Washington University, St. Louis, MO 63130, USA |
| |
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. |
| |
Keywords: | anodic amide oxidation TRH-R bicyclic lactum peptidomimetics |
本文献已被 ScienceDirect 等数据库收录! |