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

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

Research output: Contribution to journalArticle

5 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)8510-8523
Number of pages14
JournalJournal of Organic Chemistry
Volume78
Issue number17
DOIs
StatePublished - Sep 6 2013
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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    Ha, K., Lebedyeva, I. O., Li, Z., Martin, K., Williams, B., Faby, E., Nasajpour, A., Pillai, G. G., Al-Youbi, A. O., & Katritzky, A. R. (2013). Conformationally assisted lactamizations for the synthesis of symmetrical and unsymmetrical bis-2,5-diketopiperazines. Journal of Organic Chemistry, 78(17), 8510-8523. https://doi.org/10.1021/jo401235k