Russian Chemical Bulletin p. 98 - 99 (1993)
Update date:2022-08-03
Topics: Synthesis Enantiomer Chiral center Stereochemistry Enantioselective synthesis Optical rotation Chemical Synthesis Reaction Mechanism Chirality
Odinokov, V. N.
Ishmuratov, G. Yu.
Kharisov, R. Ya.
Serebryakov, E. P.
Tolstikov, G. A.
An optically active juvenile hormone analogue, S-(+)-methoprene (1), is synthesized in six steps from technical grade S-(+)-3,7-dimethyl-1,6-octadiene (''(+)-dihydromyrcene'', e.e. ca. 50percent) by a novel procedure which begins with selective hydroalumination-oxidation to give S-(-)-citronellol.This alcohol is oxidized to give S-(-)-citronellal which on reaction with allylmagnesium chloride affords 6S,10-dimethyl-1,9-undecadien-4R/S-ol (5).Smidt-Moiseev oxygenation of 5 followed by dehydration leads to 6S,10-dimethyl-3E,9-undecadien-2-one.The latter on treatment with isopropoxyethynylmagnesium bromide is transformed into isopropyl 3,7S,11-trimethyl-2E/Z,4E,10-dodecatrienoate which upon Brown solvomercuration-reduction in MeOH gives 1 in 14percent overall yield.
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