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Pheromones of coleoptera. Communication 6. Synthesis of R,Z-14-methyl-8-hexadecenal (cis-trogodermal)

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

Conclusions

The simple synthesis of optically active R,Z-14-methyl-8-hexadecenal (cis-trogodermal), the principal components of the aggregation pheromone ofTrogoderma granarium, was accomplished. The synthesis was based on the use of R-1-bromo-4-methylhexane and Z-4-chloro-2-buten-1-ol as the sources of the chiral and olefin fragments.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 906–910, April, 1987.

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Hao, N.K., Mavrov, M.V. & Serebryakov, É.P. Pheromones of coleoptera. Communication 6. Synthesis of R,Z-14-methyl-8-hexadecenal (cis-trogodermal). Russ Chem Bull 36, 833–837 (1987). https://doi.org/10.1007/BF00962333

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  • DOI: https://doi.org/10.1007/BF00962333

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