Abstract
Dodec-8Z-en-1-ol (VIII) and tetradec-8Z-en-1-ol (IX) and the corresponding acetates (X and IX) — components of the sex pheromones of many species of Lepidoptera — have been synthesized from cyclooctene (I) in three stages. The ozonolysis of (I) (−70°C, CH2Cl2-MeOH, NaHCO3; −20°C, Ac2O/Et3N) led to methyl 8-oxooctanoate (II). The DNPH of (II), (III), mp 59–61°C. The coupling of (II) with n-C3H17 CH=PPh3 (IV) or with n-C5H11 CH=PPh3 (V) (−70°C, 2 h; 25°C, 15 h, Ar) gave the methyl esters of dodec-8Z-enoic (VI) and tetradec-8Z-enoic (VII) acids, respectively. The reduction of (VI) and (VII) [(i-Bu)2AlH, 0°C, 2 h; 25°C, 15 h] gave the corresponding alcohols (VIII) and (IX) by the acetylation (Ac2O-Py, 25°C, 24 h) of which, (X) and (XI), were obtained. The yields (%): (II) 80, (VI) 45, (VII) 60, (VIII) 95, (IX) 90, (X) 75, (XI) 74. The IR and PMR spectra of compounds (II) and (VI–XI) are given.
Similar content being viewed by others
Literature cited
S. L. Schreiber, R. E. Claus, and J. Reagan, Tetrahedron Lett.,23, No. 38, 3867 (1982).
G. A. Tolstikov, V. N. Odinokov, M. S. Miftakhov, R. I. Galeeva, F. A. Valeev, N. N. Sidorov, R. S. Mukhametzyanova, and G. Yu. Ishmuratov, Zh. Org. Khim.,18, No. 4, 721 (1982).
V. N. Odinokov, R. I. Galeeva, O. V. Sokol'skaya, G. A. Dzhemileva, and G. A. Tolstikov, Dokl. Akad. Nauk SSSR,280, No. 3, 646 (1985).
S. Li, G. Wei, B. Chen, and D. Yan, Youji Huaxne (Org. Chem.), No. 6, p. 466 (1986).
V. N. Odinokov, G. Yu. Ishmuratov, R. I. Galeeva, R. Ya. Kharisov, O. V. Sokol'skaya, R. S. Mukhametzyanova, T. A. Kargapol'tseva, and G. A. Tolstikov, Zh. Org. Khim.,24, No. 4, 719 (1988).
V. N. Odinokov, L. P. Botsman, N. A. Nagaeva, and G. A. Tolstikov, Zh. Org. Khim.,24, No. 1, 80 (1988).
H. J. Bestmann and O. Vostrowsky, in: Chemie der Pflanzenschutz and Schädlingsbekämpfungsmittel (ed. R. Wegler), Springer, Berlin (1981).
A. J. Gordon and R. A. Ford, The Chemist's Companion, Wiley-Interscience (1972) [Russian translation, Mir, Moscow (1976), p. 302].
J. W. Cooper, Spectroscopic Techniques for Organic Chemists, Wiley, New York (1980).
V. I. Odinokov, V. R. Akhmetova, G. A. Tolstikov, A. M. Moiseenkov, and A. V. Semenovskii, Zh. Org. Khim.,21, No. 3, 489 (1985).
F. C. Pennington, W. D. Celmer, W. M. McLamore, V. V. Bogert, and I. A. Solomons, J. Am. Chem. Soc.,75, 109 (1953).
V. N. Odinokov, V. R. Akhunova, R. S. Bakeeva, R. I. Galeeva, A. V. Semenovskii, A. M. Moiseenkov, and G. A. Tolstikov, Zh. Org. Khim.,13, 532 (1977).
M. Horuke, M. Tanouchi, and C. Hirano, Agr. Biol. Chem.,44, No. 2, 257 (1980).
Additional information
Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 276–279, March–April, 1989.
Rights and permissions
About this article
Cite this article
Odinokov, V.N., Akhmetova, V.R., Khasanov, K.D. et al. Pheromones of insects and their analogs. Chem Nat Compd 25, 240–243 (1989). https://doi.org/10.1007/BF00598421
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00598421