66007-19-0Relevant academic research and scientific papers
A practical total synthesis of both e - And Z -isomers of optically pure (S)-14-methylhexadec-8-enal (Trogodermal)
Yadav, Jhillu S.,Chandravathi,Thrimurtulu,Prasad,Ghamdi, Ahmad Alkhazim Al
, p. 1513 - 1518 (2013/07/05)
The total synthesis of both E- and Z-isomers of optically pure (S)-14-methylhexadec-8-enal (trogodermal) is described. Key steps involved Corey-Fuchs reaction, zipper isomerization, and different hydrogenation conditions for cis- and trans-isomers. Georg
Pheromone synthesis. Part 240: Cross-metathesis with Grubbs I (but not Grubbs II) catalyst for the synthesis of (R)-trogodermal (14-methyl-8-hexadecenal) to study the optical rotatory powers of compounds with a terminal sec-butyl group
Mori, Kenji
experimental part, p. 3900 - 3909 (2009/09/08)
(R)-Trogodermal (14-methyl-8-hexadecenal), the sex pheromone of Trogoderma species of pest insects against stored products, and its (S)-isomer were synthesized by using olefin cross-metathesis between (R)- or (S)-7-methyl-1-nonene and 8-nonenyl acetate as the key step. This step was successful with Grubbs I but not with Grubbs II catalyst. The latter caused randomization of the carbon skeleton to give a mixture of abnormal products with both longer or shorter carbon chains than the desired product. The specific rotations of 18 newly and 6 previously synthesized compounds with a terminal sec-butyl group were measured to conclude them to be [α]D +3.5 to +6.5 or -3.6 to -6.4.
A facile synthesis of (S)-trogodermal
Chattopadhay, S.,Mamdapur, V. R.,Chadha, M. S.
, p. 848 - 849 (2007/10/02)
A simple route for the synthesis of (S)-(Z)- and (S)-(E)-14-methyloctadec-8-en-1-al (Ia and Ib) has been developed.The achiral acetylene (9) is alkylated with the chiron bromide (S)-5 in the presence of BuLi as the base to give 10.This on subsequent functionalisation furnishes both Ia and Ib.
