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タイトル: Gold(I)-Catalyzed Cascade Cyclization of Alkynyl Indoles for the Stereoselective Construction of the Quaternary Carbon Center of Akuammiline Alkaloids
著者: Hashimoto, Naoki
Taguchi, Junichi
Arichi, Norihito  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0003-3618-4959 (unconfirmed)
Inuki, Shinsuke  KAKEN_id  orcid https://orcid.org/0000-0002-7525-1280 (unconfirmed)
Ohno, Hiroaki  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-3246-4809 (unconfirmed)
著者名の別形: 橋本, 直季
田口, 淳一
有地, 法人
井貫, 晋輔
大野, 浩章
キーワード: Column chromatography
Cyclization
Lipids
Mixtures
Organic compounds
発行日: 15-Dec-2023
出版者: American Chemical Society (ACS)
誌名: The Journal of Organic Chemistry
巻: 88
号: 24
開始ページ: 17306
終了ページ: 17321
抄録: A gold-catalyzed cyclization reaction of alkynyl-indoles has been developed for the stereoselective construction of the quaternary carbon center of fused indolines. This reaction efficiently produces fused indolines via diastereoselective 6-endo-dig cyclization controlled by a bulky TIPS group, followed by nucleophilic attack of the carboxy group on the resulting imine. The lactone moiety of the fused indoline can be reductively cleaved to produce a tricyclic indoline, which could be useful for the synthesis of akuammiline alkaloids.
著作権等: This document is the Accepted Manuscript version of a Published Work that appeared in final form in 'The Journal of Organic Chemistry', 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/acs.joc.3c02142
The full-text file will be made open to the public on December 5, 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/2433/286469
DOI(出版社版): 10.1021/acs.joc.3c02142
PubMed ID: 38051730
出現コレクション:学術雑誌掲載論文等

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