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Bioinspired Syntheses of Seven Macrodiolide Analogs of Aplysiatoxin by the Late-Stage Functionalization of a Dehydroaplysiatoxin Derivative
http://hdl.handle.net/2237/0002012968
http://hdl.handle.net/2237/00020129683e848d25-b8b1-4782-899f-15a1d13b5276
| 名前 / ファイル | ライセンス | アクション |
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JOC_hada2025_revised05a.pdf (596 KB)
Download is available from 2026/6/13.
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| アイテムタイプ | itemtype_ver1(1) | |||||||||
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| 公開日 | 2025-07-28 | |||||||||
| タイトル | ||||||||||
| タイトル | Bioinspired Syntheses of Seven Macrodiolide Analogs of Aplysiatoxin by the Late-Stage Functionalization of a Dehydroaplysiatoxin Derivative | |||||||||
| 言語 | en | |||||||||
| 著者 |
Hada, Kohei
× Hada, Kohei
× Nishikawa, Toshio
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| アクセス権 | ||||||||||
| アクセス権 | embargoed access | |||||||||
| アクセス権URI | http://purl.org/coar/access_right/c_f1cf | |||||||||
| 権利 | ||||||||||
| 権利情報 | This document is the Accepted Manuscript version of a Published Work that appeared in final form in [The Journal of Organic Chemistry], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [https://pubs.acs.org/articlesonrequest/AOR-5WCME2ABTTIWHGEWTTP5].” | |||||||||
| 言語 | en | |||||||||
| 内容記述 | ||||||||||
| 内容記述タイプ | Abstract | |||||||||
| 内容記述 | Aplysiatoxin (ATX) is a bioactive polyketide natural product produced by cyanobacteria and characterized by macrodiolide and spiroacetal moieties. Many structurally diverse analogs of ATX have been reported but are little studied due to the minuscule quantities in which they have been isolated. We hypothesized that most of these analogs are biosynthesized from anhydroATX, a dehydrated form of ATX, and report a de novo synthesis of the phenolic OMe ether of anhydro-deBr-ATX, as well as syntheses of seven macrodiolide ATX analogs, OTX-B1, B2, M, J, and neo-deBr-ATX-A, G, and J, according to the biosynthetic hypothesis. One of the highlights is our synthesis of neo-deBr-ATX-G by a radical cascade reaction involving 1,5-HAT and an intramolecular conjugate addition to efficiently construct its novel bicyclic structure. This work resulted in revisions to the configurations of OTX-B1, B2, and neo-deBr-ATX-G, and the ring structure of OTX-M. | |||||||||
| 言語 | en | |||||||||
| 出版者 | ||||||||||
| 出版者 | ACS Publications | |||||||||
| 言語 | en | |||||||||
| 言語 | ||||||||||
| 言語 | eng | |||||||||
| 資源タイプ | ||||||||||
| 資源タイプresource | http://purl.org/coar/resource_type/c_6501 | |||||||||
| タイプ | journal article | |||||||||
| 出版タイプ | ||||||||||
| 出版タイプ | AM | |||||||||
| 出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||||||
| 関連情報 | ||||||||||
| 関連タイプ | isVersionOf | |||||||||
| 識別子タイプ | DOI | |||||||||
| 関連識別子 | https://doi.org/10.1021/acs.joc.5c00651 | |||||||||
| 収録物識別子 | ||||||||||
| 収録物識別子タイプ | PISSN | |||||||||
| 収録物識別子 | 0022-3263 | |||||||||
| 書誌情報 |
en : The Journal of Organic Chemistry 巻 90, 号 23, p. 7786-7792, 発行日 2025-06-13 |
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| ファイル公開日 | ||||||||||
| 日付 | 2026-06-13 | |||||||||
| 日付タイプ | Available | |||||||||
