caa a22 4500 465765866 CHVBK 20180323111913.0 cr unu---uuuuu 170327e19901201xx s 000 0 eng 10.1007/BF02535904 doi (NATIONALLICENCE)springer-10.1007/BF02535904 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 [Elektronische Daten] [J. George Pomonis, Heldur Hakk] 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 KMnO4 and 18-crown-6 ether. American Oil Chemists' Society, 1990 George Pomonis J. Insect Biochemistry and Physiology, Biosciences Research Laboratory, ARS-USDA, State University Station, P.O. Box 5674, 58105, Fargo, ND aut Hakk Heldur Insect Biochemistry and Physiology, Biosciences Research Laboratory, ARS-USDA, State University Station, P.O. Box 5674, 58105, Fargo, ND aut Lipids Springer-Verlag 25/12(1990-12-01), 821-826 0024-4201 25:12<821 1990 25 11745 https://doi.org/10.1007/BF02535904 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02535904 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- George Pomonis J. Insect Biochemistry and Physiology, Biosciences Research Laboratory, ARS-USDA, State University Station, P.O. Box 5674, 58105, Fargo, ND aut NATIONALLICENCE 700 1- Hakk Heldur Insect Biochemistry and Physiology, Biosciences Research Laboratory, ARS-USDA, State University Station, P.O. Box 5674, 58105, Fargo, ND aut NATIONALLICENCE 773 0- Lipids Springer-Verlag 25/12(1990-12-01), 821-826 0024-4201 25:12<821 1990 25 11745 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer