Synthesis of diaryl ether components of ellagitannins using ortho-quinone with consonant mesomeric effects

Synthesis of diaryl ether components of ellagitannins using ortho-quinone with consonant mesomeric effects

Methods for synthesizing C-O digallate structures, the basic unit of diaryl ether components of natural ellagitannins, are described. In the designed building block derived from gallic acid, consonantly overlapped mesomeric effects enhanced its electrophilicity. This building block demonstrated subs...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2020-04, Vol.56 (28), p.3991-3994
Hauptverfasser: Konishi, Hayato, Hirokane, Tsukasa, Hashimoto, Hajime, Ikeuchi, Kazutada, Matsumoto, Shintaro, Wakamori, Shinnosuke, Yamada, Hidetoshi
Format: Artikel
Sprache:eng
Schlagworte:
Diaryl ethers
Gallic acid
Quinones
Synthesis
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Zusammenfassung:Methods for synthesizing C-O digallate structures, the basic unit of diaryl ether components of natural ellagitannins, are described. In the designed building block derived from gallic acid, consonantly overlapped mesomeric effects enhanced its electrophilicity. This building block demonstrated substantial reactivity to improve the synthesis of dehydrodigalloyl, tergalloyl, and valoneoyl groups.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc00889c