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Synthesis of an Ellagitannin Component, the Macaranoyl Group with a Tetra-ortho-Substituted Diaryl Ether Structure

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Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/82528

Title: Synthesis of an Ellagitannin Component, the Macaranoyl Group with a Tetra-ortho-Substituted Diaryl Ether Structure
Authors: Hashimoto, Hajime Browse this author
Ishimoto, Takayuki Browse this author
Konishi, Hayato Browse this author
Hirokane, Tsukasa Browse this author
Wakamori, Shinnosuke Browse this author
Ikeuchi, Kazutada Browse this author →KAKEN DB
Yamada, Hidetoshi Browse this author
Issue Date: 4-Sep-2020
Publisher: American Chemical Society
Journal Title: Organic letters
Volume: 22
Issue: 17
Start Page: 6729
End Page: 6733
Publisher DOI: 10.1021/acs.orglett.0c02066
Abstract: Herein, a practical synthesis of the macaranoyl group contained in ellagitannins, i.e., a C-O digallate structure with a tetra-ortho-substituted diaryl ether bond, is described. The methodology involved an oxa-Michael addition/elimination reaction between a brominated ortho-quinone monoketal and a phenol with a hexahydroxydiphenoyl moiety in the presence of 18-crown-6 under dark conditions, followed by reductive aromatization. The existence of rotamers originating from the constructed ether moiety is discussed as well.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see https://pubs.acs.org/doi/10.1021/acs.orglett.0c02066
Type: article (author version)
URI: http://hdl.handle.net/2115/82528
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 池内 和忠

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