ArticleJournal of the American Chemical Society2021
Total Synthesis of (-)-Glionitrin A and B Enabled by an Asymmetric Oxidative Sulfenylation of Triketopiperazines.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- Synthetic Routes to, Stabilities and Transformations of, and Characterization of (Carbamoyl)disulfanyl Chlorides and Related CompoundsMolecules (Basel, Switzerland) · 2025Article
- Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-SizedOrganic letters · 2023Article
- Article
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3 authors.
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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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