Formation of a novel heterocyclic system based on natural alantolactone
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Natural sesquiterpene lactones which contain an exocyclic methylene group in the β-position of the lactone ring react readily with N-nucleophiles to give compounds having novel forms of biological activity when compared with the starting compounds [ 1]. When the reaction was carried out with 5α-epoxyalantolactone ( 1) (a secondary metabolite of the plant genus Inula L. [ 2]) and the tryptamine derivatives 2a,b we were able to show the formation of the novel heterocyclic system, namely the hydrogenated benzo[ g]furo[4,3,2- cd]indolones 3a,b.
Keywordsepoxyalantolactone 9a-hydroxy-1-[2-(1 H-indol-3-yl)ethyl]-5a,9-dimethyldodecahydro-benzo[g]furo[4,3,2-cd]indol-3(1 H)-ones tryptamines Michael reaction
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