Synthesis of novel 1,2,3-triazole-substituted tomentosins

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Abstract

A series of 1,2,3-triazole-containing tomentosin scaffolds was obtained from tomentosin 1. The synthesis involved a Michael addition of trimethylsilylazide on the α-methylene-γ-lactone function of the natural sesquiterpene lactone 1 to give the diastereoisomers 2 and 3, which were readily separated by column chromatography. These compounds underwent copper-catalyzed Huisgen 1,3-dipolar cycloaddition with various terminal alkynes to provide compounds 4a–h and 5a–h in good yields.

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Zaki, M., Oukhrib, A., El Hakmaoui, A., Hiebel, M. A., Berteina-Raboin, S., & Akssira, M. (2019). Synthesis of novel 1,2,3-triazole-substituted tomentosins. Zeitschrift Fur Naturforschung - Section B Journal of Chemical Sciences, 74(3), 273–281. https://doi.org/10.1515/znb-2018-0225

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