Selenium dioxide promoted selenylation/cyclization of leucosceptrane sesterterpenoids.

Chem Commun (Camb)

Key Laboratory of Phytochemistry and Natural Medicines, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.

Published: September 2024

A novel selenium dioxide promoted selenylation/cyclization of leucosceptrane sesterterpenoids was reported. Two types of leucosceptrane derivatives with different valence states of selenium atoms (Se and Se) were obtained. The mechanisms of these two processes were proposed, and the selenium-containing derivates may serve as intermediates of Riley oxidation that could be trapped with appropriate substrates. Immunosuppressive activity screening revealed that 10 and 11 had obvious inhibitory effects on IFN-γ production, with IC values of 5.29 and 17.60 μM, respectively, which were more active than their precursor leucosceptroid A.

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http://dx.doi.org/10.1039/d4cc03674cDOI Listing

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