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.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No 1, pp. 110–112, January, 1993.
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Odinokov, V.N., Ishmuratov, G.Y., Kharisov, R.Y. et al. Synthesis ofS-(+)-hydroprene. Russ Chem Bull 42, 100–101 (1993). https://doi.org/10.1007/BF00699985
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DOI: https://doi.org/10.1007/BF00699985