Premium
Synthesis of cis and trans methyl 8‐ and 13‐octadecenoate‐d 2 and d 4 isomers
Author(s) -
Adlof R. O.,
Miller W. R.,
Emken E. A.
Publication year - 1978
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.2580150175
Subject(s) - chemistry , wittig reaction , deuterium , triphenylphosphine , cis–trans isomerism , alkyl , medicinal chemistry , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics
The synthesis of deuterium labelled, unsaturated, isomeric fatty acids was required for a series of triple‐labelled feeding experiments. The preparation of the cis and trans isomers of methyl 8‐octadecenoate‐17, 18‐d 2 , methyl 8‐octadecenoate‐13, 13, 14, 14‐d 4 , methyl 13‐octadecenoate‐17, 18‐d 2 and methyl 13‐octadecenoate‐17, 17, 18, 18‐d 4 is described. The syntheses utilize tris (triphenylphosphine) ‐ chlororhodium(I) catalyst for the incorporation of deuterium. The double bond is introduced by coupling a deuterated alkyl triphenylphosphonium salt with the appropriate aldehydic ester using the Wittig reaction. Optimization of conditions has increased the overall yields for these syntheses to ∼50% and the isotopic purity to >95%.