Abstract
Syntheses are developed for 2S-tridecyl- and 2S-tridec-10E-enylacetates, sex pheromones of the fruit flyDrosophila mulleri and the Hessian flyMayetiola destructor, respectively, that are based on ethyl-3S-hydroxybutanoate, a product from enzymatic reduction of ethyl acetoacetate by the soil yeast strain “80-1”.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
D. Enders and A. Plant,Liebigs Ann. Chem.,11, 1241 (1991).
F. Hitze and D. Hoppe,Synthesis,12, 1216 (1992).
A. S. Gopalan and H. K. Jacobs,Tetrahedron Lett.,31, 5575 (1990).
Y. Naoshima, M. Kamezawa, H. Tachibana, Y. Munakata, T. Fujita, K. Kihara, and T. Raku,J. Chem. Soc., Perkin Trans. I,5, 557 (1993).
M. Kamezawa, H. Tachibana, T. Ohtani, and Y. Naoshima,Biosci. Biotechnol. Biochem.,57, 1962 (1993).
Y. Takeuchi and K. Mori,Biosci. Biotechnol. Biochem.,57, 1967 (1993).
J. G. Millar, S. P. Foster, and M. O. Harris,J. Chem. Ecol.,17, 2437 (1991).
V. N. Odinokov, G. Yu. Ishmuratov, O.V. Sokol'skaya, I. M. Ladenkova, L. Yu. Gubaidullin, R. R. Muslukhov, and G. A. Tolstikov,Khim. Prir. Soedin., 145 (1993).
A. I. Meyers and R. A. Amos,J. Am. Chem. Soc.,102, 870 (1980).
K. Mori,Tetrahedron,37, 1341 (1981).
K. Mori and K. Tanida,Tetrahedron,37, 3221 (1981).
L. I. Zakharkin and E. A. Petrushkina,Zh. Org. Khim.,18, 1623 (1982).
Author information
Authors and Affiliations
Additional information
Work performed under the auspices of the Federal program “Integratsiya” of the RF (Contract No. A 0005).
Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 167–169, March–April, 2000.
Rights and permissions
About this article
Cite this article
Kharisov, R.Y., Petukhova, N.I., Davletova, A.R. et al. Insect pheromones and their analogs. LX. Stereocontrolled synthesis of sex pheromones ofDrosophila mulleri andMayetiola destructor . Chem Nat Compd 36, 210–212 (2000). https://doi.org/10.1007/BF02236433
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02236433