73264-89-8Relevant 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.
A CONVENIENT SYNTHESIS OF (11E,13E)-11,13-HEXADECADIENAL AND (11Z,13E)-HEXADECADIENAL
Lo, Veng Meng,Shiao, Min-Jen
, p. 1647 - 1656 (2007/10/02)
A simple method for synthesizing (11E,13E)-11,13-hexadecadienal 7, a component of the female sex pheromone of cabbage webworm, and its geometrical isomer (11Z,13E)-11,13-hexadecadienal 8 is described.
Synthesis of (Z,Z)-11,13-Hexadecadienal, a Principal Component of Navel Orangeworm (Pamyelois transitella) Pheromone
Bishop, Clyde E.,Morrow, Gary W.
, p. 657 - 660 (2007/10/02)
This report outlines a commercial synthetic process for (Z,Z)-11,13-hexadecadienal (navel orangeworm pheromone).The synthetic scheme which is employed introduces the stereochemically labile conjugated diene moiety at a late stage in the synthesis, thereby avoiding complications during the purification of intermediates.In addition, the aldehyde function is generated through a Grignard reaction sequence, obviating the generally accepted techniques which are usually unsuitable for commercial preparations.We have also observed the first reported selective inclusion by urea of a conjugated (Z,Z)-diene as a means of mild purification of labile dienic pheromone intermediates.