680202-74-8Relevant academic research and scientific papers
11,16 Oxetane lactones. Spectroscopic evidences and conformational analysis
Macías, Francisco A.,Vi?olo, Victor M.I.,Fronczek, Frank R.,Massanet, Guillermo M.,Molinillo, José M.G.
, p. 7747 - 7755 (2007/10/03)
Sesquiterpene lactones constitute a wide group of compounds with several biological activities, including allelopathic. The naturally occurring sesquiterpene lactones dehydrocostuslactone and cynaropicrin have been modified in three different ways: preparation of 11,13-oxetane lactones, addition of a second Michael acceptor and reduction of the α-methylene-γ-lactone in order to future structure-activity relationship (SAR) studies. We have obtained all oxetane lactones stereoisomers at C-11 and C-16 positions. This fact has allowed us to establish some correlations between experimental data, derived by NMR and X-ray analysis, and the configuration at C-11 and C-16, which could be a useful tool to establish the stereochemistry as well as to confirm the presence of an oxetane ring on similar compounds. Comparative conformational analyses as a key aspect in the biological behaviour of those compounds in future structure-activity relationship (SAR) studies are presented.
