Conformationally assisted lactamizations for the synthesis of symmetrical and unsymmetrical bis-2,5-diketopiperazines

Khanh Ha; Iryna Lebedyeva; Zhiliang Li; Kristin Martin; Byron Williams; Eric Faby; Amir Nasajpour; Girinath G Pillai; Abdulrahman O Al-Youbi; Alan R Katritzky

doi:10.1021/jo401235k

Conformationally assisted lactamizations for the synthesis of symmetrical and unsymmetrical bis-2,5-diketopiperazines

J Org Chem. 2013 Sep 6;78(17):8510-23. doi: 10.1021/jo401235k. Epub 2013 Aug 26.

Authors

Khanh Ha¹, Iryna Lebedyeva, Zhiliang Li, Kristin Martin, Byron Williams, Eric Faby, Amir Nasajpour, Girinath G Pillai, Abdulrahman O Al-Youbi, Alan R Katritzky

Affiliation

¹ Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA.

PMID: 23895184
DOI: 10.1021/jo401235k

Abstract

Open-chain N-Cbz-protected-peptidoyl benzotriazolides are converted by a novel lactamization strategy using proline as a turn introducer into both symmetrical (5a-c and 11a-c) and unsymmetrical (19a-e) bis-2,5-diketopiperazines (bis-2,5-DKPs), previously recognized as difficult targets.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Diketopiperazines / chemical synthesis*
Diketopiperazines / chemistry
Lactams / chemistry*
Models, Molecular
Molecular Conformation
Molecular Structure

Substances

Diketopiperazines
Lactams