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Transformations de terpénoïdes : 1. Réarrangements moléculai res et réactions d’oxydation de dérivés du longipinène, 2. Hémisynthèse de labdanes diterpénoïdes

Abstract : Chemical transformations were performed on terpenoids isolated from plants of the Asteraceae fami ly belonging to the flora of the Venezuelan Andes. From Stevia lucida Lagasca was obtained the sesquiterpene 7β,9α-dihydroxylongipin-2-en-1-one. The study of the reactivity of this compound led to the synthesis of two products resulting from oxidation reactions, and six products resulting from molecular rearrangements. Among these six rearrangement products, two new compounds, merida-2,7-dien-1,9-dione and 1-oxo-2-en-uladan-7(9)-ol ida, were characterized; these terpenes, whose carbone skeletons are unprecedented, were named Meridane and Uladane. From Oxylobus glanduliferus and Austroeupatorium inulaefolium, respectively, were isolated two diterpenes, labdan-8α,15-diol and austroeupatol . These compounds were chemically derivatized by acylation with diversely substituted aromatic carboxylic acids. The seventeen aromatic esters thus synthesized were then evaluated for their antibacterial activity.
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Pablo Armando Chacón Morales. Transformations de terpénoïdes : 1. Réarrangements moléculai res et réactions d’oxydation de dérivés du longipinène, 2. Hémisynthèse de labdanes diterpénoïdes. Chimie organique. Université de Bordeaux; Universidad de los Andes (Mérida, Venezuela), 2017. Français. ⟨NNT : 2017BORD0903⟩. ⟨tel-01827244⟩

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