Abstract
A new pathway has been proposed for the synthesis of the ethyl ester of 3,7,11-trimethyl-2,4-dodecadienoate (juvenoid hydroprene) from available 4-methyltetra-hydropyran. The cleavage of the latter to 3-methyl-5-bromo-1-acetoxypentane and coupling with isobutylmagnesium bromide gave tetrahydrogeraniol, which was oxidized to the corresponding aldehyde. The reaction of this aldehyde with allylmagnesium chloride and subsequent oxidation by O2/PdCl2-CuCl led to 6,10-dimethyl-3E-undecen-2-one, which was converted by a known method to the desired product as a mixture of 70% 2E,4E- and 30% 2Z,4E-stereoisomers. The yield of hydroprene in the six-step synthesis was 32% relative to 4-methyltetrahydropyran.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1923–1925, August, 1989.
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Odinokov, V.N., Ishmuratov, G.Y., Kharisov, R.Y. et al. Synthesis of ethyl 3,7,11-trimethyl-2,4-dodecadienoate (hydroprene) from 4-methyltetrahydropyran. Russ Chem Bull 38, 1768–1770 (1989). https://doi.org/10.1007/BF00956974
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DOI: https://doi.org/10.1007/BF00956974