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 Citations (Scopus)

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

Fingerprint

Diketopiperazines
Proline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Conformationally assisted lactamizations for the synthesis of symmetrical and unsymmetrical bis-2,5-diketopiperazines. / Ha, Khanh; Lebedyeva, Iryna Oleksandrivna; Li, Zhiliang; Martin, Kristin; Williams, Byron; Faby, Eric; Nasajpour, Amir; Pillai, Girinath G.; Al-Youbi, Abdulrahman O.; Katritzky, Alan R.

In: Journal of Organic Chemistry, Vol. 78, No. 17, 06.09.2013, p. 8510-8523.

Research output: Contribution to journalArticle

Ha, K, Lebedyeva, IO, Li, Z, Martin, K, Williams, B, Faby, E, Nasajpour, A, Pillai, GG, Al-Youbi, AO & Katritzky, AR 2013, 'Conformationally assisted lactamizations for the synthesis of symmetrical and unsymmetrical bis-2,5-diketopiperazines', Journal of Organic Chemistry, vol. 78, no. 17, pp. 8510-8523. https://doi.org/10.1021/jo401235k
Ha, Khanh ; Lebedyeva, Iryna Oleksandrivna ; Li, Zhiliang ; Martin, Kristin ; Williams, Byron ; Faby, Eric ; Nasajpour, Amir ; Pillai, Girinath G. ; Al-Youbi, Abdulrahman O. ; Katritzky, Alan R. / Conformationally assisted lactamizations for the synthesis of symmetrical and unsymmetrical bis-2,5-diketopiperazines. In: Journal of Organic Chemistry. 2013 ; Vol. 78, No. 17. pp. 8510-8523.
@article{8e2ca6e63d644abc83f9e7e2ae38739a,
title = "Conformationally assisted lactamizations for the synthesis of symmetrical and unsymmetrical bis-2,5-diketopiperazines",
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.",
author = "Khanh Ha and Lebedyeva, {Iryna Oleksandrivna} and Zhiliang Li and Kristin Martin and Byron Williams and Eric Faby and Amir Nasajpour and Pillai, {Girinath G.} and Al-Youbi, {Abdulrahman O.} and Katritzky, {Alan R.}",
year = "2013",
month = "9",
day = "6",
doi = "10.1021/jo401235k",
language = "English (US)",
volume = "78",
pages = "8510--8523",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "17",

}

TY - JOUR

T1 - Conformationally assisted lactamizations for the synthesis of symmetrical and unsymmetrical bis-2,5-diketopiperazines

AU - Ha, Khanh

AU - Lebedyeva, Iryna Oleksandrivna

AU - Li, Zhiliang

AU - Martin, Kristin

AU - Williams, Byron

AU - Faby, Eric

AU - Nasajpour, Amir

AU - Pillai, Girinath G.

AU - Al-Youbi, Abdulrahman O.

AU - Katritzky, Alan R.

PY - 2013/9/6

Y1 - 2013/9/6

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84883754242&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84883754242&partnerID=8YFLogxK

U2 - 10.1021/jo401235k

DO - 10.1021/jo401235k

M3 - Article

C2 - 23895184

AN - SCOPUS:84883754242

VL - 78

SP - 8510

EP - 8523

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 17

ER -