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Synthesis of an Ellagitannin Component, the Macaranoyl Group with a Tetra-ortho-Substituted Diaryl Ether Structure
| 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)
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Submitter: 池内 和忠
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