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j.rechem.2023.100912.pdf | 523.18 kB | Adobe PDF | 見る/開く |
タイトル: | Synthesis of 8β-hydroxy-9(11),13-abietadien-12-one from (+)-dehydroabietylamine and its AhR ligand activity |
著者: | Nishino, Katsutoshi Someya, Kenta Tsukano, Chihiro https://orcid.org/0000-0002-9361-0857 (unconfirmed) Ishikawa, Toshio Nagao, Masaya https://orcid.org/0000-0003-4006-0633 (unconfirmed) |
著者名の別形: | 西野, 勝俊 染谷, 健太 塚野, 千尋 永尾, 雅哉 |
キーワード: | Abietane diterpenoid Aryl hydrocarbon receptor Safer reagent |
発行日: | Jan-2023 |
出版者: | Elsevier BV |
誌名: | Results in Chemistry |
巻: | 5 |
論文番号: | 100912 |
抄録: | 8β-Hydroxy-9(11), 13-abietadien-12-one (1), an abietane diterpenoid and an aryl hydrocarbon receptor (AhR) ligand, was synthesized in six steps from commercially available (+)-dehydroabietylamine (2). We used the hypervalent iodine catalyst phenyliodine dicarboxylate, a safer alternative to toxic organoselenide reagents, for the oxidative dearomatization of ferruginol (7) to compound 1. Compounds 1 and 2, as well as the synthetic intermediates (compounds 3–7), were evaluated for AhR ligand activity. Only compounds 1 and 7 were active, which suggests that AhR affinity is influenced by the steric environment around the C-18 position of these compounds. |
著作権等: | © 2023 The Author(s). Published by Elsevier B.V. This is an open access article under the CC BY-NC-ND license. |
URI: | http://hdl.handle.net/2433/284479 |
DOI(出版社版): | 10.1016/j.rechem.2023.100912 |
出現コレクション: | 学術雑誌掲載論文等 |
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