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Total Synthesis of (−)-Glionitrin A and B Enabled by an Asymmetric Oxidative Sulfenylation of Triketopiperazines

Koning, Nicolas R. ; Sundin, Anders P. LU and Strand, Daniel LU (2021) In Journal of the American Chemical Society 143(50). p.21218-21222
Abstract

Asymmetric construction of dithiodiketopiperazines on otherwise achiral scaffolds remains a pivotal synthetic challenge encountered in many biologically significant natural products. Herein, we report the first total syntheses of (−)-glionitrin A/B and revise the absolute configurations. Emerging from the study is a novel oxidative sulfenylation of triketopiperazines that enables asymmetric formation of dithiodiketopiperazines on sensitive substrates. The concise route paves the way for further studies on the potent antimicrobial and antitumor activities of glionitrin A and the intriguing ability of glionitrin B to inhibit invasive ability of cancer cells.

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author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of the American Chemical Society
volume
143
issue
50
pages
5 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • pmid:34808045
  • scopus:85120353987
ISSN
0002-7863
DOI
10.1021/jacs.1c10364
project
Development of an Asymmetric Synthesis of Glionitrin A and B
language
English
LU publication?
yes
additional info
Publisher Copyright: © 2021 The Authors. Published by American Chemical Society
id
ac3e89d4-6a57-429c-9199-326981317b0f
date added to LUP
2022-01-24 09:21:39
date last changed
2024-07-14 02:36:42
@article{ac3e89d4-6a57-429c-9199-326981317b0f,
  abstract     = {{<p>Asymmetric construction of dithiodiketopiperazines on otherwise achiral scaffolds remains a pivotal synthetic challenge encountered in many biologically significant natural products. Herein, we report the first total syntheses of (−)-glionitrin A/B and revise the absolute configurations. Emerging from the study is a novel oxidative sulfenylation of triketopiperazines that enables asymmetric formation of dithiodiketopiperazines on sensitive substrates. The concise route paves the way for further studies on the potent antimicrobial and antitumor activities of glionitrin A and the intriguing ability of glionitrin B to inhibit invasive ability of cancer cells.</p>}},
  author       = {{Koning, Nicolas R. and Sundin, Anders P. and Strand, Daniel}},
  issn         = {{0002-7863}},
  language     = {{eng}},
  month        = {{12}},
  number       = {{50}},
  pages        = {{21218--21222}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of the American Chemical Society}},
  title        = {{Total Synthesis of (−)-Glionitrin A and B Enabled by an Asymmetric Oxidative Sulfenylation of Triketopiperazines}},
  url          = {{http://dx.doi.org/10.1021/jacs.1c10364}},
  doi          = {{10.1021/jacs.1c10364}},
  volume       = {{143}},
  year         = {{2021}},
}