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ISSN 0012-5008, Doklady Chemistry, 2009, Vol. 426, Part 2, pp. 138–142. © Pleiades Publishing, Ltd., 2009. Original Russian Text © A.V. Belovodskii, E.E. Shul’ts, M.M. Shakirov, G.A. Tolstikov, 2009, published in Doklady Akademii Nauk, 2009, Vol. 426, No. 6, pp. 762–765. CHEMISTRY Sesquiterpene Metylenelactones in a Palladium-Catalyzed Cross-Coupling Reaction A. V. Belovodskii, E. E. Shul’ts, M. M. Shakirov, and Academician G. A. Tolstikov Received January 27, 2009 DOI: 10.1134/S001250080906007X Compounds containing an α-methylene-γ-lactone have not been involved in reactions with organometalic fragment, in particular sesquiterpene lactones, have reagents until now. attracted attention for the past 50 years owing to their We established for the first time that isoalantolac- diverse physiological activity, including antitumor tone 1 is a reactive alkene component in the palladium- properties [1]. The biological activity of sesquiter- catalyzed cross-coupling reaction with aryl halides (the pene lactones are known to result from their behavior Heck reaction [9]). The reaction of compound 1 with 4- as alkylating agents. These compounds can form in iodoanisole, 4-iodoveratrole, or 2-iodothioanisole in vivo adducts with nucleophilic regions of biomole- DMF in the presence of catalytic amounts of palladium cules (like products of the Michael reaction with free acetate and tris(o-tolyl)phosphine and triethylamine
Doklady Chemistry – Springer Journals
Published: Jun 18, 2009
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