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Syntheses of radioactive furan fatty acids
Author(s) -
Rahn Curtis H.,
Sand Donald M.,
Krick Thomas P.,
Glass Robert L.,
Schlenk Hermann
Publication year - 1981
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02534963
Subject(s) - furan , chemistry , ring (chemistry) , elongation , organic chemistry , stereochemistry , medicinal chemistry , materials science , metallurgy , ultimate tensile strength
A novel route for the synthesis of naturally occurring furan fatty acids with particular emphasis on labeling with 14 C is described. Methyl [2‐ 14 C] 9‐(5‐pentyl‐3,4‐dimethyl‐2‐furyl)nonanoate was synthesized from 3,4‐dimethyl‐2‐pentylfuran by a new route. [3‐ 14 C]11‐(5‐Pentyl‐3‐methyl‐2‐furyl)undecanoate and [2‐ 14 C] 9‐(5‐pentyl‐2‐furyl)nonanoate were prepared from their lower homologs. The label was introduced in all cases by means of the Arndt‐Eistert method for chain elongation, using 14 CH 2 N 2 . Comparisons of yields show that, with increasing number of substituents on the ring, the furan compounds are increasingly subject to uncontrollable side reactions.