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Two geometrical isomers of linoleic acid: Improved total syntheses
Author(s) -
Ofsuki Tetsuo,
Brooker Robert F.,
Funk Max O.
Publication year - 1986
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/bf02534443
Subject(s) - chemistry , yield (engineering) , propargyl alcohol , acetylene , organic chemistry , alcohol , carbon fibers , catalysis , materials science , metallurgy , composite number , composite material
Abstract The total syntheses of 9(Z),12(E)‐ and 9(E),12(Z)‐octadecadienoic acids have been carried out. A useful intermediate in both syntheses, 8‐bromo‐octanoic acid, recently has become available from commercial sources. This compound has been used to expedite the preparation of these isomers. The remaining carbon atoms were derived from propargyl alcohol along with either 1‐heptyne or acetylene and 1‐bromopentane. Because the overall yield for each sequence was roughly 15% and there were no extraordinary reaction conditions in any of the synthetic steps, the compounds could be prepared readily in multiple gram quantities. The syntheses of the two compounds were supported by data from a variety of spectroscopic techniques.