Conclusions
The synthesis of the juvenoid methoprene and its 2Z,4E isomer (as a ∼1∶1 mixture) has been accomplished, one of the steps being the electrochemical reduction of a 3,5-dialkylthiophene-2-carboxylic acid.
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Literature cited
K. Sláma, M. Romaňuk, and F. Šorm, Insect Hormones and Bioanalogues, Springer-Verlag, New York (1974).
C. A. Henrick, G. B. Staal, and J. B. Sidall, J. Agr. Food Chem.,21, 354 (1973).
C. A. Henrick, W. E. Willy, J. W. Baum, T. A. Baer, B. A. Garcia, T. A. Mastre, and S. M. Chang, J. Org. Chem.,40, 1 (1975).
V. S. Mikhailov, V. P. Gul'tyai, S. G. Mairanovskii, S. Z. Taits, I. V. Proskurovskaya, and Yu. G. Dubovik, Izv. Akad. Nauk SSSR, Ser. Khim., 888 (1975).
V. P. Gul'tyai, I. V. Proskurovskaya, T. Ya. Rubinskaya, A. V. Lozanova, A. M. Moiseenkov, and A. V. Semenovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1576 (1979).
S. D. McGregor and D. M. Lemal, J. Am. Chem. Soc.,88, 2858 (1966).
R. M. Kellogg and W. L. Prins, J. Org. Chem.,39, 2366 (1974).
J. M. McIntosh and R. A. Sieler, J. Org. Chem.,43, 4431 (1978).
O. V. Shekhter, Yu. S. Tsizin, and E. A. Pridantseva, Zh. Obshch. Khim.,45, 1186 (1975).
W. G. Blenderman and M. M. Joullié, Synth. Commun.,11, 881 (1981).
S. D. Sharma, S. Singh, and S. S. Bari, Indian J. Chem.,14B, 379 (1976).
B. S. Kulkarni and A. S. Rao, Org. Prep. Proc. Int.,10, 73 (1978).
V. Jarolim and F. Šorm, Coll. Czech. Chem. Commun.,39, 587 (1974).
V. Ramanathan and R. Levine, J. Org. Chem.,27, 1667 (1962).
M. G. Reinecke, H. W. Adickes, and C. Pyum, J. Org. Chem.,36, 2690 (1971).
S. D. Andrews, A. C. Day, P. Raymond, and M. C. Whiting, Org. Synth.,50, 27 (1970).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1370–1373, June, 1983.
The authors thank E. A. Pridantseva for the gift of a sample of methoprene, and Z. G. Isaeva for valuable discussions of the results.
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Lozanova, A.V., Gul'tyai, V.P., Karaseva, A.N. et al. Synthesis of methoprene via electroreduction of the thiophene ring. Russ Chem Bull 32, 1241–1245 (1983). https://doi.org/10.1007/BF00953165
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DOI: https://doi.org/10.1007/BF00953165