New Synthetic Method for the Racemic form of the Bean Weevil Acanthoscelides obtectus Male Pheromone

New Synthetic Method for the Racemic form of the Bean Weevil Acanthoscelides obtectus Male Pheromone 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 [3] from male bean weevil Acanthoscelides obtectus (Say). Now, several syntheses of this compound are known [1]. 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 http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry of Natural Compounds Springer Journals

New Synthetic Method for the Racemic form of the Bean Weevil Acanthoscelides obtectus Male Pheromone

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Publisher
Springer Journals
Copyright
Copyright © 2018 by Springer Science+Business Media, LLC, part of Springer Nature
Subject
Pharmacy; Pharmacy; Organic Chemistry; Plant Sciences
ISSN
0009-3130
eISSN
1573-8388
D.O.I.
10.1007/s10600-018-2429-5
Publisher site
See Article on Publisher Site

Abstract

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 [3] from male bean weevil Acanthoscelides obtectus (Say). Now, several syntheses of this compound are known [1]. 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

Journal

Chemistry of Natural CompoundsSpringer Journals

Published: Jun 7, 2018

References

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