Bioinspired Total Synthesis of (−)‐Vescalin: A Nonahydroxytriphenoylated <i>C</i>‐Glucosidic Ellagitannin

Richieu, Antoine; Peixoto, Philippe A.; Pouységu, Laurent; Deffieux, Denis; Quideau, Stéphane

doi:10.1002/anie.201707613

Cited by 28 publications

(22 citation statements)

References 58 publications

(30 reference statements)

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“…The synthesis of ETs is much more complex than that of EA, has relatively small yields and poses a major challenge: generating stereoselective linkages of galloyl-derived biphenyl moieties across different sites of the glucose core [ 1 ]. Nevertheless, several total syntheses have been reported over the years [ 90 , 91 , 92 , 93 , 94 ].…”

Section: Production Of Ellagic Acidmentioning

confidence: 99%

Recent Advances in the Production and Applications of Ellagic Acid and Its Derivatives. A Review

2020

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Ellagitannins (ETs), characterized by their diversity and chemical complexity, belong to the class of hydrolysable tannins that, via hydrolysis under acidic or alkaline conditions, can yield ellagic acid (EA). They are mostly found as a part of extractives in angiosperms. As known antioxidants and chelators, EA and EA derivatives are drawing an increasing interest towards extensive technical and biomedical applications. The latter ones include possible antibacterial, antifungal, antiviral, anti-inflammatory, hepato- and cardioprotective, chemopreventive, neuroprotective, anti-diabetic, gastroprotective, antihyperlipidemic, and antidepressant-like activities, among others. EA’s synthesis and production challenges prompt further research on new methods and alternative sources. Conventional and prospective methods and raw materials for the production of EA and its derivatives are reviewed. Among the potential sources of EA, the residues and industrial streams of the pulp industry have been highlighted and considered as an alluring alternative in terms of commercial exploitation.

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Section: Production Of Ellagic Acidmentioning

confidence: 99%

Recent Advances in the Production and Applications of Ellagic Acid and Its Derivatives. A Review

2020

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“…This process is known to underlie the biosynthetic origin of the macrocycle 10 and is a classic example of C–H functionalization logic applied to synthesis. 11 Since Barton’s first example of this type of reactivity, 12 many methods have become available for oxidative phenolic coupling, including the use of organic oxidants, 13 stoichiometric 13b , 14 and catalytic 15 metal oxidants, and electrochemical oxidation. 16 Additional precedence for intramolecular oxidative coupling of short peptides is provided in the Evans group’s efforts toward the synthesis of vancomycin.…”

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confidence: 99%

Scalable Access to Arylomycins via C–H Functionalization Logic

2018

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Arylomycins are a promising class of “latent” antibacterial natural products currently in preclinical development. Access to analogues within this family has previously required a lengthy route involving multiple functional group manipulations that is costly and time-intensive on scale. This study presents a simplified route predicated on simple C–H functionalization logic that is enabled by a Cu-mediated oxidative phenol coupling that mimics the putative biosynthesis. This operationally simple macrocyclization is the largest of its kind and can be easily performed on gram scale. The application of this new route to a formal synthesis of the natural product and a collection of new analogues along with their biological evaluation is also reported.

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“…Consequently, the structures of castalagin and vescalagin were revised, resulting in the latest structures. In 2017, Quideau synthesized the latest structure of vescalin [ 83 ].…”

Section: Structural Revision In Ellagitanninsmentioning

confidence: 99%

“…Quideau’s synthesis of vescalin was achieved by the development of a novel method for synthesizing the NHTP group ( Figure 39 ) [ 83 ]. The six-step transformation of 100 provided 101 that possessed the ( S )-HHDP group between O-2 and O-3.…”

Section: Structural Revision In Ellagitanninsmentioning

confidence: 99%

Structural Revisions in Natural Ellagitannins

et al. 2018

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Ellagitannins are literally a class of tannins. Triggered by the oxidation of the phenolic parts on β-pentagalloyl-d-glucose, ellagitannins are generated through various structural conversions, such as the coupling of the phenolic parts, oxidation to highly complex structures, and the formation of dimer and lager analogs, which expand the structural diversity. To date, more than 1000 natural ellagitannins have been identified. Since these phenolic compounds exhibit a variety of biological activities, ellagitannins have potential applications in medicine and health enhancement. Within the context of identifying suitable applications, considerations need to be based on correct structural features. This review describes the structural revisions of 32 natural ellagitannins, namely alnusiin; alnusnin A and B; castalagin; castalin; casuarinin; cercidinin A and B; chebulagic acid; chebulinic acid; corilagin; geraniin; isoterchebin; nobotanin B, C, E, G, H, I, J, and K; punicalagin; punicalin; punigluconin; roxbin B; sanguiin H-2, H-3, and H-6; stachyurin; terchebin; vescalagin; and vescalin. The major focus is on the outline of the initial structural determination, on the processes to find the errors in the structure, and on the methods for the revision of the structure.

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Bioinspired Total Synthesis of (−)‐Vescalin: A Nonahydroxytriphenoylated C‐Glucosidic Ellagitannin

Cited by 28 publications

References 58 publications

Recent Advances in the Production and Applications of Ellagic Acid and Its Derivatives. A Review

Recent Advances in the Production and Applications of Ellagic Acid and Its Derivatives. A Review

Scalable Access to Arylomycins via C–H Functionalization Logic

Structural Revisions in Natural Ellagitannins

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