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タイトル: | Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso‐Cyclization |
著者: | Takeuchi, Haruka Inuki, Shinsuke https://orcid.org/0000-0002-7525-1280 (unconfirmed) Nakagawa, Kohei Kawabe, Takaaki Ichimura, Atsuhiko https://orcid.org/0000-0003-0366-5211 (unconfirmed) Oishi, Shinya Ohno, Hiroaki https://orcid.org/0000-0002-3246-4809 (unconfirmed) |
著者名の別形: | 井貫, 晋輔 川邊, 隆彰 市村, 敦彦 大石, 真也 大野, 浩章 |
キーワード: | alkaloids natural products photocatalysis radical ipso-cyclization total synthesis |
発行日: | 16-Nov-2020 |
出版者: | Wiley |
誌名: | Angewandte Chemie |
巻: | 59 |
号: | 47 |
開始ページ: | 21210 |
終了ページ: | 21215 |
抄録: | We report herein a nonbiomimetic strategy for the total synthesis of the plicamine‐type alkaloids zephycarinatines C and D. The key feature of the synthesis is a stereoselective reductive radical ipso‐cyclization using visible‐light‐mediated photoredox catalysis. This cyclization enabled the construction of a 6, 6‐spirocyclic core structure through the addition of a carbon‐centered radical onto the aromatic ring. Biological evaluation of zephycarinatines and their derivatives revealed that the synthetic derivative with a keto group displays moderate inhibitory activity against LPS‐induced NO production. This approach could offer future opportunities to expand the chemical diversity of plicamine‐type alkaloids as well as providing useful intermediates for their syntheses. |
著作権等: | This is the peer reviewed version of the following article: ['Angewandte Chemie - International Edition', 59(47), 21210-21215], which has been published in final form at https://doi.org/10.1002/anie.202009399. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. The full-text file will be made open to the public on 11 September 2021 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. 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。 This is not the published version. Please cite only the published version. |
URI: | http://hdl.handle.net/2433/259186 |
DOI(出版社版): | 10.1002/anie.202009399 |
PubMed ID: | 32770565 |
出現コレクション: | 学術雑誌掲載論文等 |
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