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7546429 
Journal Article 
SYNTHESIS OF S-(+)-HYDROPRENE 
Odinokov, VN; Ishmuratov, GY; Kharisov, RY; Serebryakov, EP; Tolstikov, GA 
1993 
1 
Russian Chemical Bulletin
ISSN: 1066-5285
EISSN: 1573-9171 
42 
1 
100-101 
WOS:A1993MM95700023 
A novel path to S-(+)-hydroprene (1) starting from the technical grade S-(+)-dihydromyrcene (2, e.e. greater-than-or-equal-to 50%) 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 SE-6,10-dimethyl-3-undecen-2-one (7) which was treated with ethoxyethynylmagnesium bromide to give the title juvenile hormone analogue in approximately 23% overall yield.