New synthesis of (11Z,13Z)-11,13-hexadecadienal, the female sex pheromone of the navel orangeworm.
Kenji Mori
文献索引:Biosci. Biotechnol. Biochem. 73(12) , 2727-30, (2009)
全文:HTML全文
摘要
(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.
相关化合物
相关文献:
2015-06-01
[Mol. Pharm. 12 , 2010-8, (2015)]
2014-11-01
[Anim. Behav. 98 , 79-85, (2014)]
1998-11-30
[Ann. N. Y. Acad. Sci. 855 , 511-3, (1998)]
2002-08-01
[J. Econ. Entomol. 95(4) , 692-8, (2002)]
2000-06-01
[Bull. Entomol. Res. 90(3) , 183-90, (2000)]