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Macrocyclic lactones as a source for radiohalogenated fatty acid analogs and their precursors

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Abstract

A simple approach is presented whereby omega halogenated fatty acids can be obtained from macrocyclic musk lactones which are industrially available. While providing a secure source of 16-iodo-hexadecanoic acid and 17-iodo-heptadecanoic acid, the scheme allows ready access to a large number of untried fatty acid analogs. Examples presented are 16-iodo-hexadecanoic acid. 16-iodo-7-hexadecenoic acid. 16-iodo-12-oxa-hexadecanoic acid, 15-iodo-pentadecanoic acid, and 15-iodo-12-keto-pentadecanoic acid.

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References

  1. N. D. POE, G. D. ROBINSON, N. S. MacDONALD, Proc. Soc. Exp. Med., 148 (1975) 215.

    Google Scholar 

  2. G. D. ROBINSON, Intern. J. Appl. Radiation Isotopes, 28 (1977) 149.

    Google Scholar 

  3. H. J. MACHULLA, G. STOCKLIN, C. KUPFERNAGEL et al., J. Nucl. Med., 19 (1978) 298.

    PubMed  Google Scholar 

  4. H. R. SCHON, H. R. SCHELBERT, G. D. ROBINSON et al., Am. Heart J., 103 (1982) 532.

    PubMed  Google Scholar 

  5. H. R. SCHON, H. R. SCHELBERT, A. NAJAFI, et al., Am. Heart J., 103 (1982) 548.

    PubMed  Google Scholar 

  6. H. R. SCHELBERT, E. HENZE, M. E. PHELPS et al., Am. Heart J., 103 (1982) 588.

    PubMed  Google Scholar 

  7. E. E. VAN DER WALL, Dissertation, Vrije Universiteit Te Amsterdam, 1981.

  8. H. J. MACHULLA, M. MARSMANN, K. DUTSCHKA, Eur. J. Nucl. Med., 5 (1980) 171.

    PubMed  Google Scholar 

  9. G. W. KABALKA, E. E. GOOCH, C. OTTO, J. Radioanal. Chem., 65 (1981) 115.

    Google Scholar 

  10. G. STOCKLIN, G. KLOSTER, Metabolic Analogue Tracers, in Computed Emission Tomography, P. J. ELL, B. L. HOLMAN (Eds), Oxford U. Press, 1982, p. 299.

  11. H. J. MACHULLA, Radioactive Labelling of Fatty Acids for Metabolic Studies, in Applications of Nuclear and Radiochemistry, R. M. LABRECHT, N. MORCOS (Eds), Pergamon Press, 1982, p. 325.

  12. F. F. KNAPP, M. M. GOODMAN, A. P. CALLAHAN et al., J. Med. Chem., 26 (1983) 1293.

    PubMed  Google Scholar 

  13. M. ARGENTINI, M. ZAHNER, P. A. SCHUBIGER, J. Radioanal. Chem., 65 (1981) 131.

    Google Scholar 

  14. P. R. STORY, P. BUSCH, Adv. Org. Chem., 8 (1972) 67.

    Google Scholar 

  15. T. G. BACK, Tetrahedron 33 (1977) 3041.

    Google Scholar 

  16. K. C. NICOLAOU, Tetrahedron, 33 (1977) 683.

    Google Scholar 

  17. G. OHLOFF, Fortschr. Chem. Forsch., 12 (1969) 185.

    Google Scholar 

  18. S. ABE, T. ETO, Y. TSUJITO, Koryo, 96 (1970) 19.

    Google Scholar 

  19. S. ABE, T. ETO, Y. TSUJITO, Cosmetics and Perfumery, 88 (1973)67.

    Google Scholar 

  20. S. ABE, Koryo, 135 (1982) 37.

    Google Scholar 

  21. P. Z. BEDOUKAIN, Perfumery and Flavor Synthetics, Second ed., Elsevier, New York, 1967, p. 248.

    Google Scholar 

  22. L. RŮZIĆKA, Helv. Chim. Acta, 9 (1926) 230.

    Google Scholar 

  23. L. RŮZIĆKA, Helv. Chim. Acta, 9 (1926) 715.

    Google Scholar 

  24. M. KERSCHBAUM, Ber., 60B (1927) 902.

    Google Scholar 

  25. E. W. SANAGEL, W. H. CAROTHERS, J. Am. Chem. Soc., 57 (1935) 929.

    Google Scholar 

  26. E. W. SANAGEL, W. H. CAROTHERS, J. Am. Chem. Soc., 58 (1936) 654.

    Google Scholar 

  27. G. OHLOFF, J. BECKER, K. H. SCHULTE-ELTE, Helv. Chim. Acta, 50 (1967) 705.

    Google Scholar 

  28. A. ESCHENMOSER, D. FELIX, G. OHLOFF, Helv. Chim. Acta, 50 (1967) 708.

    Google Scholar 

  29. H. NOZAKI, T. MORE, R. NOYORI, Tetrahedron Letters, 9 (1967) 779.

    Google Scholar 

  30. K. A. BAUER, A. K. KÖRBER, Old and New Macrocyclic Musks: A General Review from the Industrial Standpoint, in Fragrance and Flavor Substances, R. CROTEAU (Ed.) D. and PS Verlag, 3017 Pattensen 1, West Germany, 1980, p. 129.

    Google Scholar 

  31. J. J. BECKER, United States Patent 3,890,353 Issued 17 June 1975.

  32. R. HOPP, K. BAUER, West Germany Patent 24 10 859 Issued 18 September 1975.

  33. F. IMAIZUMI, K. GOTO, K. SEKINE, Japanese Patent 78 90,284. Issued August 8, 1978.

  34. F. IMAIZUMI, K. GOTO, K. SEKINE, Japanese Patent 78 90,283. Issued August 8, 1978.

  35. K. BAUER, A. KÖRBER, K. H. BORK, West Germany Patent 29 29 864, Issued 19 February 1981.

  36. H. HUNSDIECKER, Ber., 76B (1943) 142.

    Google Scholar 

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Dougan, H., Lyster, D.M. & Vincent, J.S. Macrocyclic lactones as a source for radiohalogenated fatty acid analogs and their precursors. Journal of Radioanalytical and Nuclear Chemistry, Articles 89, 71–78 (1985). https://doi.org/10.1007/BF02070205

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  • DOI: https://doi.org/10.1007/BF02070205

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