Russian Chemical Bulletin p. 100 - 101 (1993)
Update date:2022-08-11
Topics:
Odinokov, V. N.
Ishmuratov, G. Yu.
Kharisov, R. Ya.
Serebryakov, E. P.
Tolstikov, G. A.
A novel path to S-(+)-hydroprene (1) starting from the technical grade S-(+)-dihydromyrcene (2, e.e. > 50percent) is proposed.The latter was selectively transformed into S-3,7-dimethyloctanal (5) in three steps including hydroalumination.The reactions of 5 with allyl- or methallylmagnesium chloride followed, respectively, either by oxygenation in the presence of PdCl2/CuCl or by ozonolysis, afford S,E-6,10-dimethyl-3-undecen-2-one (7) which was treated with ethoxyethynylmagnesium bromide to give the title juvenile hormone analogue in ca. 23percent overall yield.
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