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Biosci Biotechnol Biochem

Title:		"New synthesis of (11Z,13Z)-11,13-hexadecadienal, the female sex pheromone of the navel orangeworm"
Author(s):		Mori K;
Address:		"Photosensitive Materials Research Center, Toyo Gosei Co., Ltd., Inba-gun, Chiba, Japan. kjk-mori@arion.ocn.ne.jp"
Journal Title:		Biosci Biotechnol Biochem
Year:		2009
Volume:		20091207
Issue:		12
Page Number:		2727 - 2730
DOI:		10.1271/bbb.90611
ISSN/ISBN:		1347-6947 (Electronic) 0916-8451 (Linking)
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"
Keywords:		Aldehydes/*chemical synthesis/chemistry Animals Female Lepidoptera/*chemistry Sex Attractants/*chemical synthesis/chemistry;
Notes:		"MedlineMori, Kenji eng Research Support, Non-U.S. Gov't England 2009/12/08 Biosci Biotechnol Biochem. 2009 Dec; 73(12):2727-30. doi: 10.1271/bbb.90611. Epub 2009 Dec 7"