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  • New synthesis of (11Z,13Z)-11,13-hexadecadienal, the female sex pheromone of the navel orangeworm.

New synthesis of (11Z,13Z)-11,13-hexadecadienal, the female sex pheromone of the navel orangeworm.

Bioscience, biotechnology, and biochemistry (2009-12-08)
Kenji Mori
ABSTRACT

(11Z,13Z)-11,13-hexadecadienal, the female sex pheromone of the navel orangeworm (Amyelois transitella), was synthesized from commercially available 10-bromo-1-decanol in a 27% overall yield (8 steps). The synthesis was achieved by using 10-iododecanal, trimethylsilylacetylene and (Z)-1-bromo-1-butene as the key building blocks, employing Sonogashira-Hagihara coupling and Brown's hydroboration-protonolysis as the key reactions. The terminal formyl group was installed in the earlier stage of the synthesis rather than in the final step. This procedure enabled the multi-gram-scale preparation of this economically important pheromone.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
cis-11-Hexadecenal, 95%
Sigma-Aldrich
10-Bromo-1-decanol, technical grade, 90%