Abstract
Ethyl 5,8,11,14-eicosatetraenoate-19,19,20,20-d 4 and ethyl 8,11,14-eicosatrienoate-19,19,20,20-d 4 were synthesized by Grignard coupling of the methanesulfonyl ester of 2,5-undecadiyn-1-ol-10,10,11,11-d 4 with 5,8-nonadiynoic acid and 8-nonynoic acid, respectively. The coupled products upon Lindlar reduction, followed by the preparation of their ethyl esters, yielded deuteriated ethyl arachidonate and ethyl dihomo-γ-linolenate, which were completely characterized by13C and1H nuclear magnetic resonance and mass spectral analysis.
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Abbreviations
- GLC:
-
gas-liquid chromatography
- NMR:
-
nuclear magnetic resonance
- THF:
-
tetrahydrofuran
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Luthria, D.L., Sprecher, H. Synthesis of ethyl arachidonate-19,19,20,20-d 4 and ethyl dihomo-γ-linolenate-19,19,20,20-d 4 . Lipids 28, 853–856 (1993). https://doi.org/10.1007/BF02536242
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DOI: https://doi.org/10.1007/BF02536242