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Synthesis 1992; 1992(12): 1239-1241
DOI: 10.1055/s-1992-26348
short paper
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Pheromones; 87.1 An Efficient Synthesis of (6E,11Z)-6,11-Hexadecadienyl Acetate and (6E,11Z)-6,11-Hexadecadienal: Female Sex Pheromone Components of Antheraea pernyi and A. polyphemus (Lepidoptera: Saturniidae)

Hans Jürgen Bestmann* , Neelakanthi E. Gunawardena
  • *Institut für Organische Chemie der Universität Erlangen-Nürnberg Henkesstraße 42, D-8520 Erlangen, Germany
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Publikationsdatum:
29. April 2002 (online)

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(6E,11Z)-Hexadecadienyl acetate (15) and the corresponding aldehyde 16, the female sex pheromone components of Antheraea pernyi and A. polyphemus (Lepidoptera; Saturniidae) have been synthesized in 32 % and 27 % overall yields, respectively, and in 99 % isomeric purity. Tetrahydropyran (1) was used as the starting material to obtain 5-bromopentanol (3) which was subsequently chain elongated to 7-(tetrahydropyran-2-yloxy)-1-heptyne (5) by the standard procedures. The organolithium compound from 5 was coupled with (Z)-1-bromo-4-nonene (11), obtained from the Wittig reaction between pentyltriphenylphosphonium bromide (9) and 4-(tetrahydropyran-2-yloxy)butanal (8) followed by bromination. The product, (Z)-1-(tetrahydropyran-2-yloxy)-11-hexadecen-6-yne (12) which resulted, was reduced with sodium/liquid ammonia to give 13 with the E-6 bond. Removal of the protecting group resulted in the desired alcohol 14 which on acetylation and oxidation gave the desired acetate 15 and the aldehyde 16, respectively.