73264-90-1Relevant articles and documents
New synthesis of (11Z,13Z)-11,13-Hexadecadienal, the female sex pheromone of the navel orangeworm
Mori, Kenji
experimental part, p. 2727 - 2730 (2010/09/11)
(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-12-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.
Highly Stereoselective Synthesis of Acetates of Mono and Diunsaturated Alcohols and Analogous Aldehydes, Components of Lepidopteran Sex Pheromones, using Tetrakis-palladium
Michelot, Didier
, p. 130 - 134 (2007/10/02)
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