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
Publication statusPublished - Sep 6 2013
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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