Synthesis of [14,14,14-²H₃] 12-hydroxytetradecanoic acid and [13,14-²H₂] 11-hydroxytetradecanoic acid useful as tracers to study a (11E)-desaturation reaction in Spodoptera littoralis

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• 作者：Navarro ; Isabel ; Fabriá ; s ; Gemma ; Camps ; Francisco
• 关键词：Sex pheromone ; biosynthesis ; mass labeling ; hydroxyfatty acid ; Spodoptera littoralis
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：1996
• 出版时间：March, 1996
• 年：1996
• 卷：4
• 期：3
• 页码：439-443
• 全文大小：427 K

文摘

The synthesis of deuterium labeled 11- and 12-hydroxytetradecanoic acids to study a (11E) desaturase in the mothSpodoptera littoralis is reported. [14,14,14-²H₃] 12-hydroxytetradecanoic acid was synthesized in four steps from 11-iodo-1-undecene in 49 % overall yield. Deuterium was introduced by reaction of an epoxy ester with (CD₃)₂CuLi. The preparation of [13,14-²H₂] 11-hydroxytetradecanoic acid was carried out in six steps from 11-bromoundecanoic acid in 55 % overall yield. In this case, label was introduced by deuteration of an homoallyl alcohol with D₂, using the Wilkinson catalyst. Incubation of pheromone glands with either of both acids did not lead to the formation of the labeled (11E)-tetradecenoic acid.