Abstract
A convergent synthesis of octadeca-2E, 13Z-dienyl acetate, a pheromone component ofSynanthedon tipuliformis C., has been developed. The synthesis is based on cross-coupling of 8-iodooct-2E-en-I-ol THP ether with dec-5Z-enyl bromide catalyzed by CuBr.
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References
A. M. Sorochinskaya and B. G. Kovalev,Khim Prir. Soedin., 1989, 264 [Chem. Nat. Compd., 1989 (Engl. Transl.)].
A. M. Sorochinskaya, and B. G. Kovalev,Zh. Org. Khim., 1991,27, 722 [J. Org. Chem. USSR, 1991,27 (Engl. Transl.)].
M. Schwarz, J. Klun, B. A. Leonhardt, and D. T. Johnson,Tetrahedron Lett., 1983,24, 722.
F. Ramiandrasoa, C. Descoins, Domaine de Brouessy, and Magny-les-Hameaux,Synth. Commun., 1989,19, 2703.
V. N. Odinokov, G. Yu. Ishmuratov, I. M. Ladenkova, O. V. Sokol'skaya, R. R. Muslukhov, V. R. Akhmetova, E. V. Gorobets, A. V. Kuchin, and G. A. Tolstikov,Khim. Prir. Soedin., 1993, 749 [Chem. Nat. Compd., 1993 Engl. Transl.)].
U. M. Dzhemilev, O. S. Vostrikova, R. M. Sultanova, and A. R. Gimaeva,Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 2156 [Bull. Acad. Sci. USSR, Div. Chem. Sci, 1988,37, 1936 (Engl. Transl.)].
V. N. Odinokov, G. Yu. Ishmuratov, R. I. Galeeva, O. V. Sokol'skaya, Kh. F. Sagitdinova, and G. A. Tolstikov,Zh. Org. Khim., 1990,26, 57 [J. Org. Chem. USSR, 1990,26 (Engl. Transl.)].
G. Ohloff, C. Vial, F. Naf, and M. Pawlak,Helv. Chim. Acta, 1977,60, 1161.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1529–1531, August, 1997.
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Ishmuratov, G.Y., Yakovleva, M.P., Kharisov, R.Y. et al. A convergent synthesis of octadeca-2E, 13Z-dienyl acetate, a pheromone component ofSynanthedon tipuliformis C.. Russ Chem Bull 46, 1465–1467 (1997). https://doi.org/10.1007/BF02505687
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DOI: https://doi.org/10.1007/BF02505687