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Title: Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso‐Cyclization
Authors: Takeuchi, Haruka
Inuki, Shinsuke  kyouindb  KAKEN_id  orcid (unconfirmed)
Nakagawa, Kohei
Kawabe, Takaaki
Ichimura, Atsuhiko  kyouindb  KAKEN_id  orcid (unconfirmed)
Oishi, Shinya
Ohno, Hiroaki  kyouindb  KAKEN_id  orcid (unconfirmed)
Author's alias: 井貫, 晋輔
川邊, 隆彰
市村, 敦彦
大石, 真也
大野, 浩章
Keywords: alkaloids
natural products
radical ipso-cyclization
total synthesis
Issue Date: 16-Nov-2020
Publisher: Wiley
Journal title: Angewandte Chemie
Volume: 59
Issue: 47
Start page: 21210
End page: 21215
Abstract: 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.
Rights: 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 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'.
This is not the published version. Please cite only the published version.
DOI(Published Version): 10.1002/anie.202009399
PubMed ID: 32770565
Appears in Collections:Journal Articles

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