- Influence of N,N'-Substituents on the FeCl3-Catalyzed Photo-oxidation of 2,5-Dibenzylpiperazine-3,6-diones
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Reactions carried out on benzoyl (2) and hydroxybenzyl (10) derivatives of L-phenylalanine-cycloanhydride 1 lead to the conclusion that the structure 3, previously proposed for picroroccellin (a metabolite from the lichen Roccella fuciformis), should be r
- Barbier, Michel
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- Total Synthesis of (?)-Glionitrin A and B Enabled by an Asymmetric Oxidative Sulfenylation of Triketopiperazines
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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.
- Koning, Nicolas R.,Strand, Daniel,Sundin, Anders P.
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supporting information
p. 21218 - 21222
(2021/12/03)
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- Pyrazine Chemistry. IV. Oxidation of 3,6-Dibenzylpiperazine-2,5-diones
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The autoxidation of (+/-)cis- and trans-3,6-dibenzyl-1,4-dimethylpiperazine-2,5-diones (6) and (8) has been shown to give (+/-)-6-benzyl-1,4-dimethylpiperazine-2,3,5-trione (12).Oxidation of a (+/-)cis-trans mixture of 1,4-diacetyl-3,6-dibenzylpiperazine-
- Marcuccio, Sebastian M.,Elix, John A.
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p. 343 - 346
(2007/10/02)
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