Synthesis ofS-(+)-hydroprene |
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| Authors: | V. N. Odinokov G. Yu. Ishmuratov R. Ya. Kharisov E. P. Serebryakov G. A. Tolstikov |
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| Affiliation: | (1) Institute of Organic Chemistry, the Ural Branch, Russian Academy of Sciences, 450054 Ufa, Russian Federation;(2) N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow, Russian Federation |
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| Abstract: | A novel path toS-(+)-hydroprene (1) starting from the technical gradeS-(+)-dihydromyrcene (2, e.e.  50%) is proposed. The latter was selectively transformed intoS-3,7-dimethyloctanal (5) in three steps including hydroalumination. The reactions of5 with allyl- or methallylmagnesium chloride followed, respectively, either by oxygenation in the presence of PdCl2/CuCl or by ozonolysis, affordS,E-6,10-dimethyl-3-undecen-2-one (7) which was treated with ethoxyethynylmagnesium bromide to give the title juvenile hormone analogue in  23% overall yield.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No 1, pp. 110–112, January, 1993. |
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| Keywords: | ethylS-3,7,11-trimethyl-2E,4E-dodecadienoate, synthesis S-3,7-dimethyl-1,6-octadiene, hydroalumination S-3,7-dimethyloctanal 6S, 10-dimethyl-1-undecen-4R/S-ol 2,6S,10-trimethyl-1-undecen-4R/S-ol, ozonolysis S,E-6,10-dimethyl-3-undecen-2-one |
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