Bulletin of the Academy of Sciences of the USSR Division of Chemical Science p. 1768 - 1770 (1989)
Update date:2022-08-11
Topics:
Odinokov, V. N.
Ishmuratov, G. Yu.
Kharisov, R. Ya.
Lomakina, S. I.
Tolstikov, G. A.
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-methyltetrahydropyran.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 percent 2E,4E- and 30 percent 2Z,4E-stereoisomers.The yield of hydroprene in the six-step synthesis was 32 percent relative to 4-methyltetrahydropyran.
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