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

Author:
Zaki, Mohamed, Oukhrib, Abdelouahd, El Hakmaoui, Ahmed, Hiebel, Marie-Aude, Berteina-Raboin, Sabine, Akssira, Mohamed
Source:
Zeitschrift für Naturforschung 2019 v.74 no.3 pp. 273-281
ISSN:
1865-7117
Subject:
alkynes, chromatography, cycloaddition reactions, diastereomers, sesquiterpenoids
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.
Agid:
6322234