Abstract
(Z)-hexadec-11-enal and (Z)-hexadec-11-1-yl acetate — components of the sex pheromone of insects of the generaHeliothis andManestra, respectively — have been synthesized by the condensation of undec-10-enal with hex-1-yne, deoxygenation of the heptadec-1-en-12-yn-11-ol formed via the corresponding tosylate to heptadec-1-en-12-yne, and the selective oxonolysis of the latter.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
H. J. Bestmann and O. Vostrowsky, Chemie der Pflanzenschutz- und Schadlings-bekamp-fungsmittel, Springer, Berlin, Vol. 6 (1981), p. 29.
B. G. Kovalev, V. P. Konyukhov, and A. F. Sholl', Uch. Zap. Tartusk. Univ.,545, 91 (1980).
V. V. Buleza, S. G. Apasov, É. R. Myttus, T. M. Tashlykova, and A. S. Kovaleva, Dokl. Akad. Nauk SSSR,267, No. 1, 237 (1982).
P. M. Mistrot, L. K. Gaston, and T. C. Baker, J. Chem. Ecol.,8, No. 7, 1043 (1982).
M. M. Pope, L. K. Gaston, and T. C. Baker, Insect Physiol.,30, No. 12, 943 (1984).
B. G. Kovalev, S. F. Nedopekina, K. V. Lebedeva, and A. N. Kost, Bioorg. Khim.,5, 912 (1979).
B. G. Kovalev, S. F. Nedopekina, and A. N. Kost, Dokl. Akad. Nauk SSSR,249, 370 (1979).
US Patent No. 4042681 (1977).
G. A. Tolstikov, V. N. Odinokov, R. I. Galeeva, R. S. Bakeeva, and V. R. Akhunova, Khim. Prir. Soedin., 239 (1982).
U. M. Dzhemilev, G. G. Balezina, L. A. Volkova, V. P. Krivonogov, and G. A. Tolstikov, Khim. Prir. Soedin., 97 (1980).
H. J. Bestmann, I. Kantardjiev, P. Kösel, W. Stransky, and O. Vostrowsky, Chem. Ber.,111, 248 (1978).
H. J. Bestmann, K. H. Koschatzky, W. Schützke, J. Süb, and O. Vsotrowsky, Ann. Chem.,9, 1705 (1981).
B. G. Kovalev, E. D. Matveeva, V. V. Stan, G. A. Vovk, L. G. Yudin, and A. N. Kost, Zh. Org. Khim.,16, 2032 (1980).
A. A. Botar, A. Barabas, I. Orean, J. Csonka-Horvai, and F. Hodisan, Rev. Roum. Chim.,28, 741 (1983).
W. Seidel and H. J. Schäfer, Chem. Ber.,113, No. 12, 3898 (1980).
L. I. Zakharkin and V. V. Guseva, Khim. Prir. Soedin., 776 (1984).
V. N. Odinokov, U. M. Dzhemilev, G. Yu. Ishmuratov, L. P. Botsman, O. S. Vostrikova, I. M. Ladenkova, R. M. Sultanov, N. A. Nogaeba, and G. A. Tolstikov, Khim Prir. Soedin, No. 2, 186 (1987).
V. P. Konyukhov, B. G. Lovalev, V. A. Minyailo, V. V. Stin, and Yu. F. Oprunenko, Khemoretseptsiya Nasekomykh (Vilnius), No. 3, 37 (1978).
Additional information
Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 440–444, May–June, 1987.
Rights and permissions
About this article
Cite this article
Odinokov, V.N., Ishmuratov, G.Y., Ladenkova, I.M. et al. Insect pheromones and their analogs. Chem Nat Compd 23, 365–368 (1987). https://doi.org/10.1007/BF00600843
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00600843