Efficient synthesis of 3E,13Z-octadecadienol,its acetate, 4E,6E,11Z-hexadecatrienal,and 4E,6E,11Z-hexadecatrienyl acetate,sex pheromones of some lepidopteran species

The title linear acetogenins have been synthesized by a strategy of joining acetylcyclopropane to 8Z-tridecenol or 5Z-decenol prepared after Julia, leading to the corresponding secondary cyclopropylcarbinols. The ZnBr₂/Me₃SiBrinitiated homoallylic rearrangement of the latter assures at a key step the stereospecific construction of transoid fragments of the target molecules.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2521–2529, November, 1991.