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Synthesis of ω9‐tetracosynoic and ω9‐octacosynoic acids as entries into tritiated metabolic precursors of cis ‐9‐tricosene and cis ‐9‐heptacosene in the housefly
Author(s) -
George Pomonis J.,
Hakk Heldur
Publication year - 1990
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/bf02535904
Subject(s) - chemistry , housefly , bromide , organic chemistry , catalysis , alcohol , botany , larva , musca , biology
The syntheses of 15‐tetracosynoic acid (ω9‐tetracosynoic acid) and 19‐octacosynoic acid (ω9‐octacosynoic acid) are described. These alkynoic acids are to be tritiated to the corresponding alkenoic acids, which will be used as metabolic precursors of housefly pheromone components. The final step in each synthesis involved the coupling of 1‐decyne to the lithio‐salt of the appropriate ω‐bromoacid. Homologation of dibromoalkanes was accomplished with triphasic catalytic displacement of bromide by cyanide ion. Oxidation of a bromo‐alcohol to a bromoacid was performed in benzene with KMnO 4 and 18‐crown‐6 ether.