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Attractant pheromones of coleoptera. Communication 1. Simple synthesis of exo- and endo-brevicomins using the oxy-cope rearrangement

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

A five-stage synthesis of exo- and endo-brevicomins was carried out from acrolein and methyl vinyl ketone, with an oxy-Cope rearrangement of 4-ethyl-3-methyl-1,5-hexadien-3-ol as the key stage.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1887–1890, August, 1985.

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Serebryakov, É.P., Gamalevich, G.D. & Shekhtman, R.I. Attractant pheromones of coleoptera. Communication 1. Simple synthesis of exo- and endo-brevicomins using the oxy-cope rearrangement. Russ Chem Bull 34, 1737–1739 (1985). https://doi.org/10.1007/BF00948528

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  • DOI: https://doi.org/10.1007/BF00948528

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