Total Synthesis of (−)-Glionitrin A and B Enabled by an Asymmetric Oxidative Sulfenylation of Triketopiperazines
(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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https://lup.lub.lu.se/record/ac3e89d4-6a57-429c-9199-326981317b0f
- author
- Koning, Nicolas R. ; Sundin, Anders P. LU and Strand, Daniel LU
- organization
- publishing date
- 2021-12-22
- 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
-
- scopus:85120353987
- pmid:34808045
- 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
- 2024-09-22 09:16:00
@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}}, }