New synthesis of (11Z,13Z)-11,13-hexadecadienal, the female sex pheromone of the navel orangeworm.
(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.
Mori
Kenji
K
Photosensitive Materials Research Center, Toyo Gosei Co., Ltd., Inba-gun, Chiba, Japan. kjk-mori@arion.ocn.ne.jp
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D005260:Female; D007915:Lepidoptera / Q000737:chemistry*; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D012724:Sex Attractants; C061128:11-hexadecenal