Issue 82, 2023
From the journal:

Chemical Communications

Photo-induced scandium-catalyzed biomimetic skeleton conversion of lathyrane to naturally rare eupholathone Euphorbia diterpenes†

Jin-Bu Xu,‡ab   Peng Wen,‡a   Neng Wang,a   Xiaohuan Li,a   Jia-Hong Li,a   Steven De Jonghe,d   Dominique Schols,d   Feng-Zheng Chen*c  and  Feng Gao ORCID logo *ab  

* Corresponding authors

a School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, Sichuan, People's Republic of China
E-mail: gaof@swjtu.edu.cn

b Yibin Institute of Southwest Jiaotong University, Yibin 644000, Sichuan, People's Republic of China

c College of Chemistry, Leshan Normal University, Leshan 614004, Sichuan, People's Republic of China
E-mail: fzchen7200@163.com

d KU Leuven, Department of Microbiology, Immunology and Transplantation, Rega Institute for Medical Research, Laboratory of Virology and Chemotherapy, Herestraat 49, box 1043, Leuven 3000, Belgium

Abstract

The naturally scarce eupholathone-type euphornin E (1) was efficiently prepared from abundant lathyrane-type Euphorbia factor L1via a visible-light-induced Sc(OTf)3-catalyzed tandem process. Eupholathones 2 and 3 were also smoothly obtained by changing the reaction solvent. This route provides a convenient method for easily constructing scarce eupholathone- from lathyrane-type Euphorbia diterpenes, and confirms the biogenetic relationship between them from a chemical standpoint. Notably, compound 1 exhibited good anti-HIV activity.

Graphical abstract: Photo-induced scandium-catalyzed biomimetic skeleton conversion of lathyrane to naturally rare eupholathone Euphorbia diterpenes

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Article information

DOI
https://doi.org/10.1039/D3CC03541G
Article type
Communication
Submitted
24 Jul 2023
Accepted
17 Sep 2023
First published
19 Sep 2023

Chem. Commun., 2023,59, 12290-12293

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Photo-induced scandium-catalyzed biomimetic skeleton conversion of lathyrane to naturally rare eupholathone Euphorbia diterpenes

J. Xu, P. Wen, N. Wang, X. Li, J. Li, S. De Jonghe, D. Schols, F. Chen and F. Gao, Chem. Commun., 2023, 59, 12290 DOI: 10.1039/D3CC03541G

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