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Synthesis of fluorinated analogs of myristic acid as potential inhibitors of egyptian armyworm ( Spodoptera littorialis ) Δ 11 desaturasedesaturase
Author(s) -
Abad JoséLuis,
Villorbina Gemma,
Fabriàs Gemma,
Camps Francisco
Publication year - 2003
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-003-1137-2
Subject(s) - spodoptera littoralis , chemistry , myristic acid , stereochemistry , pyridine , biosynthesis , mythimna separata , organic chemistry , enzyme , noctuidae , biology , fatty acid , botany , larva , palmitic acid
To study the activity of the different desaturases present in the pheromone biosynthetic pathway of the Egyptian armyworm, Spodoptera littoralis , we prepared a series of mono‐and gem ‐difluorinated analogs of myristic acid with halogen substitution at the C8–C11 positions of the aliphatic chain via specifically positioned dithiane precursors. Thus, transformation of dithianes by treatment with N ‐bromosuccinimide in the presence of H 2 O followed by reduction with LiAIH 4 afforded the appropriate alcohols, which reacted with diethylaminosulfur trifluoride to give rise to the corresponding monofluoroderivative intermediates. Alternatively, the introduction of the gem ‐difluoro functionality was carried out by reaction of the appropriate dithiane intermediate with 1,3‐dibromo‐5,5‐dimethylhydantoin in the presence of HF/pyridine. The activity of these fluorinated FA as substrates and inhibitors of the desaturases involved in the biosynthesis of the sex pheromonal blend of S. littoralis has been studied. In this case, 11‐fluorotetradecanoic acid elicited a moderate inhibitory activity of Δ 11 desaturase.