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Preparation of methyl 8c, 11c‐octadecadienoate‐17,17,18,18‐d 4 and methyl 8c,11c,14c‐octadecatrienoate‐17,17,18,18‐d 4
Author(s) -
Adlof R. O.,
Emken E. A.
Publication year - 1986
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580230205
Subject(s) - chemistry , wittig reaction , triphenylphosphine , phosphonium , deuterium , halide , double bond , medicinal chemistry , catalysis , stereochemistry , organic chemistry , physics , quantum mechanics
Multi‐gram quantities of methyl 8c,11c‐octadecadienoate‐17,17,18,18‐d 4 and methyl 8c,11c,14c‐octadecatrienoate‐17,17,18,18‐d 4 were synthesized for use in human metabolism studies. The deuterium atoms were incorporated using tris(triphenylphosphine)chlororhodium (I) catalyst and deuterium gas. The double bonds in the Δ11 and Δ14 positions were incorporated by acetylenic coupling. The double bond in the Δ8 position was introduced by the Wittig coupling of the mono‐ or di‐unsaturated triphenyl phosphonium halide to 7‐formylheptanoate. The 15‐25% trans isomers formed by the Wittig coupling reaction were removed by silver resin chromatography. Overall yields were 15%, for the diene ester (an 8‐step synthesis) and 12%, for the triene (a 12‐step synthesis). Both compounds were shown to have an isotopic purity of > 97% d 4 .