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

Article abstract of DOI:10.1016/0968-0896(96)00023-5

The synthesis of deuterium labeled 11- and 12-hydroxytetradecanoic acids to study a (11E) desaturase in the moth Spodoptera 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)-tetradecanoic acid.