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A convergent synthesis of (17R,5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid analogues and their tritiated derivatives |
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| Authors: | Igor V Ivanov Stepan G RomanovValery P Shevchenko Elena A RozhkovaMikhail A Maslov Nataliya V GrozaNikolai F Myasoedov Hartmut KuhnGalina I Myagkova |
| Affiliation: | a M.V. Lomonosov State Academy of Fine Chemical Technology, Chemistry and Technology of Fine Organic Compounds, Vernadskogo Pr. 86, Moscow 119571, Russian Federation b Institute of Biochemistry, University Clinics Charité, Humboldt University, Berlin D-10117, Germany c Institute of Molecular Genetics, Kurchatov Square 2, Moscow 123182, Russian Federation d Department of Chemistry, Princeton University, Princeton, NJ 08544, USA |
| Abstract: | 17(R)-OH-AA and 14,15-dehydro-17(R)-OH-AA were synthesized from a common tetraacetylenic precursor and their azide derivatives were obtained in moderate yields via the corresponding p-toluenesulfonates. Since the azido group remained stable during tritiation procedure on Lindlar's catalyst in benzene, both 14,15-dehydro-17(S)-N3-AA and 14,15-dehydro-17(R)-OH-AA constitute useful intermediates in the synthesis of radio-labelled 17(S)-N3-AA and 17(R)-OH-AA. In contrast, reduction of azide in methanol afforded 17(S)-NH2-AA with 95% yield. |
| Keywords: | coupling reactions eicosanoids azides labelling |
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