Abstract
Natural sesquiterpene lactones which contain an exocyclic methylene group in the β-position of the lactone ring react readily with N-nucleophiles. When studying the reaction of the natural epoxyalantolactone with the primary amines we demonstrate the formation of a new heterocyclic system—the hydrogenated benzo[g]furo[4,3,2-cd]indol-3(1H)-one. Spectral data on the characteristics of the synthesized compounds are presented. The data on the reaction mechanisms and its applicability for the preparation are discussed.
Highlights
Sesquiterpene lactones are a large group of plant-derived metabolites
Sesquiterpene lactones were used as scaffolds for the synthesis of antitumor compounds (Grienke et al, 2018)
Natural sesquiterpene lactones containing the exocyclic methylene group in the β-position of the lactone cycle readily react with N-nucleophiles, including amines
Summary
Ananiev 2, Marco Avila-Rodriguez 3, Vadim V. Tarasov 4 and Gjumrakch Aliev * 1,4,5. Laboratoire de Cardio-Oncologie et Chimie Médicinale (CNRS), France. Natural sesquiterpene lactones which contain an exocyclic methylene group in the β-position of the lactone ring react readily with N-nucleophiles. When studying the reaction of the natural epoxyalantolactone with the primary amines we demonstrate the formation of a new heterocyclic system—the hydrogenated benzo[g]furo[4,3,2-cd]indol-3(1H)-one. Spectral data on the characteristics of the synthesized compounds are presented. The data on the reaction mechanisms and its applicability for the preparation are discussed
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