Synthesis of Cyclic Peptide Mimetics by the Successive Ring Expansion of Lactams. Issue 54 (9th August 2017)

• Record Type: Journal Article
• Authors: Stephens, Thomas C.; Lodi, Mahendar; Steer, Andrew M.; Lin, Yun; Gill, Matthew T.; Unsworth, William P.
• Is Part Of: Chemistry. Volume 23:Issue 54(2017)
• Page Start: 13314
• Page End: 13318
• Publication Date: 2017-08-09
• Subjects: cyclic peptides -- lactams -- macrocycles -- medium-sized rings -- ring expansion; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201703316
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A successive ring‐expansion protocol is reported that enables the controlled insertion of natural and non‐natural amino acid fragments into lactams. Amino acids can be installed into macrocycles via an operationally simple and scalable iterative procedure, without the need for high dilution. This method is expected to be of broad utility, especially for the synthesis of medicinally important cyclic peptide mimetics. Abstract : Magic rings : A successive ring‐expansion protocol is reported that enables the controlled insertion of natural and non‐natural amino acid fragments into lactams. Amino acids can be installed into macrocycles by an operationally simple and scalable iterative procedure, without the need for high dilution. This method is expected to be of broad utility, especially for the synthesis of medicinally important cyclic peptide mimetics (see scheme).