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| ファイル | 記述 | サイズ | フォーマット | |
|---|---|---|---|---|
| jacs.3c04124.pdf | 463.77 kB | Adobe PDF | 見る/開く |
| タイトル: | Total Synthesis and Structure Revision of (+)-Lancilactone C |
| 著者: | Kuroiwa, Hidetaka Suzuki, Soichiro Irie, Kazuhiro   https://orcid.org/0000-0001-7109-8568 (unconfirmed)Tsukano, Chihiro  https://orcid.org/0000-0002-9361-0857 (unconfirmed) |
| 著者名の別形: | 黒岩, 秀崇 鈴木, 総一郎 入江, 一浩 塚野, 千尋 |
| キーワード: | Chemical structure Chemical synthesis Hydrocarbons Molecular structure Organic synthesis |
| 発行日: | 12-Jul-2023 |
| 出版者: | American Chemical Society (ACS) |
| 誌名: | Journal of the American Chemical Society |
| 巻: | 145 |
| 号: | 27 |
| 開始ページ: | 14587 |
| 終了ページ: | 14591 |
| 抄録: | Lancilactone C is a tricyclic triterpenoid that inhibits human immunodeficiency virus (HIV) replication in H9 lymphocytes with no cytotoxicity. Its tricyclic skeleton comprises trans-dimethylbicyclo[4.3.0]nonane and 7-isopropylenecyclohepta-1, 3, 5-triene. The latter unique structure, in which all carbon atoms are sp2 hybridized, is not found in other triterpenoids and needs to be verified synthetically. Herein, we have accomplished the first total synthesis of lancilactone C (proposed structure) by developing a new domino [4 + 3] cycloaddition reaction involving oxidation, Diels–Alder reaction, elimination, and electrocyclization. We have also revised the structure based on the total synthesis of lancilactone C according to its plausible biosynthetic pathway. |
| 記述: | ランシラクトンCの全合成と構造改訂 --ペリ環状反応を駆使して--. 京都大学プレスリリース. 2023-06-22. Total recall on HIV: Researchers create total synthesis of HIV replication inhibitor. 京都大学プレスリリース. 2023-07-31. |
| 著作権等: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © 2023 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.3c04124. The full-text file will be made open to the public on June 16, 2024 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 |
| URI: | http://hdl.handle.net/2433/284134 |
| DOI(出版社版): | 10.1021/jacs.3c04124 |
| PubMed ID: | 37326375 |
| 関連リンク: | https://www.kyoto-u.ac.jp/ja/research-news/2023-06-22 https://www.kyoto-u.ac.jp/en/research-news/2023-07-31 |
| 出現コレクション: | 学術雑誌掲載論文等 |
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