Synthesis of methyl 11,14,17-eicosatrienoate-3,3,4,4,8,8,9,9-d8
1993
Rakoff, H.
For use in metabolic studies, methyl 11,14,17-eicosatrienoate- 3,3,4,4,8,8,9,9-d8 was prepared by Wittig coupling of 3,6- nonadienyltriphenylphosphonium iodide with methyl 11-oxoundecanoate- 3,3,4,4,8,8,9,9,-d8 in the presence of butyl lithium. The all cis isomer was separated by high-pressure liquid chromatography using a reverse-phase column. An unexpected by-product, methyl 10,13,16-nonadecatrienoate- 2,2,3,3,7,7,8,8-d8, was also isolated. The structures and the configurations of the compounds were confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry.
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