Synthesis of the insect sex pheromone of Achroia grisella via the novel synthon, 1-tetrahydro-pyranyloxy dodec 11-yne

Ranganathan, S. ; Maniktala, V. ; Kumar, Raaj (1982) Synthesis of the insect sex pheromone of Achroia grisella via the novel synthon, 1-tetrahydro-pyranyloxy dodec 11-yne Synthetic Communications, 12 (12). pp. 959-966. ISSN 0039-7911

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Official URL: http://www.tandfonline.com/doi/abs/10.1080/0039791...

Related URL: http://dx.doi.org/10.1080/00397918208061933

Abstract

We report the preparation of 1-tetrahydro-pyranyloxy dodec 11-yne(1), from castor oil, with an overall yield of 9.6%, and illustrate its use with the novel and practical synthesis of 1-oxo octadec (z) 11-ene(2), the insect sex pheromone of Achroia grisella, a species of wax moth, which are specific enemies of bees. Parenthetically, it has been found that 1 is a good precursor to the surprisingly large number of pheromones that have the structural unit, [sbnd]CH[dbnd]CH[sbnd](CH2)9CHXY2.

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