DOI 10.1007/s10600-018-2429-5 Chemistry of Natural Compounds, Vol. 54, No. 3, May, 2018 NEW SYNTHETIC METHOD FOR THE RACEMIC FORM OF THE BEAN WEEVIL Acanthoscelides obtectus MALE PHEROMONE 1* 2 I. M. Sakhautdinov, A. M. Gumerov, 1 3 A. F. Mukhametyanova, A. B. Atangulov, and M. S. Yunusov Many natural allenes and their derivatives showed cytotoxic, antibacterial, antiviral, fungicidal, and other activities [1, 2]. Herein, the synthesis of racemic pheromone methyl (R,E)-tetradeca-2,4,5-trienoate is reported. HH CO Me The pheromone methyl (R,E)-tetradeca-2,4,5-trienoate was isolated in 1970 by Horler  from male bean weevil Acanthoscelides obtectus (Say). Now, several syntheses of this compound are known . The allene motif was introduced in the early synthesis steps in all previous studies [4–9]. This complicated the task because the allene was reactive. The method proposed by us is distinctive because the allene motif is introduced in the last step using a Wittig reaction. The racemic analog of 1 was synthesized in four steps starting with commercially available methyl-4-bromocrotonate 2 and decanoic acid 3 (Scheme 1). HOOC MeO C Ph P Ph P Br CO Me 2 Cl a b CO Me CO Me 2 2 O Br Hn-C H 8 17 24 6 5
Chemistry of Natural Compounds – Springer Journals
Published: Jun 7, 2018
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