Cyclopropyl building blocks in organic synthesis, 57 - Convenient syntheses and biological activity of novel ω-trans-(bicyclopropyl)-and ω-(bicyclopropylidenyl)-substituted fatty acids and their derivatives

European Journal of Organic Chemistry

Volumn , Issue 17, 2000, Pages 2979-2989

  Löhr, Sandra ^a   Jacobi, Carsten ^a   Johann, Andre ^a   Gottschalk, Gerhard ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Bicyclopropylidene; Fatty acids; Liquid crystals; Metabolism; Reductions

Indexed keywords

BICYCLO COMPOUND; FATTY ACID DERIVATIVE;

ARTICLE; ASPERGILLUS NIDULANS; ASPERGILLUS NIGER; FATTY ACID SYNTHESIS; FUNGUS GROWTH; ORGANIC CHEMISTRY; RHODOCOCCUS;

EID: 0038277692     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200009)2000:17<2979::aid-ejoc2979>3.0.co;2-a     Document Type: Article

References (46)

1. Review: H.-W. Liu, C. T. Walsh, in The chemistry of the cyclopropyl group (Ed.: Z. Rappoport) Wiley, Chichester 1987, p. 959-1025 and references cited therein.
2. [2a] J. Salaün, M. S. Baird, Curr. Med. Chem. 1995, 2, 511-542.
3. [2b] J. Salaün, Top. Curr. Chem. 1999, 207, 1-67.
4. J. F. Toscanne, Tetrahedron 1972, 28, 363-371.
5. O. W. Thiele, Lipide, Isoprenoide mit Steroiden, Thieme, Stuttgart, 1979, p. 17-87.
6. M. Yoshida, M. Hashimoto, M. Yamashita, N. Shigematsu, M. Okuhara, M. Kosaka, K. Horikoshi, J. Antibiotics 1990, 748-754.
7. M. S. Kuo, R. J. Zielinski, J. I. Cialdella, C. K. Maschke, J. Am. Chem. Soc. 1995, 117, 10629-10634.
8. [7a] A. G. M. Barrett, G. J. Tustin, A. J. P. White, D. J. Williams, J. Chem. Soc., Chem. Commun. 1994, 1781-1782.
9. [7b] A. G. M. Barrett, G. J. Tustin, A. J. P. White, J. Williams, J. Chem. Soc., Chem. Commun. 1994, 1783-1784.
10. [7c] A. M. Barrett, J. Tustin, J. Chem. Soc., Chem. Commun. 1995, 355-356.
11. [7d] A. G. M. Barrett, W. Doubleday, K. Kasdorf, G. J. Tustin, A. J. P. White, J. Chem. Soc., Chem. Commun. 1995, 407-408.
12. A. G. M. Barrett, K. Kasdorf, G. J. Tustin, D. J. Williams, J. Chem. Soc., Chem. Commun. 1995, 1143-1144.
13. [7f] A. G. M. Barrett, A. J. P. White, D. J. Williams, J. Chem. Soc., Chem. Commun. 1995, 649-650.
14. [8a] A. G. M. Barrett, K. Kasdorf, J. Am. Chem. Soc. 1996, 118, 11030-11037.
15. [8b] G. M. Barrett, D. Hamprecht, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1996, 118, 7863-7864.
16. [8c] A. G. M. Barrett, W. W. Doubleday, G. J. Tustin, Tetrahedron 1996, 52, 15325-15338.
17. [8d] A. G. M. Barrett, W. W. Doubleday, K. Kasdorf, G. J. Tustin, J. Org. Chem. 1996, 61, 3280-3288.
18. J. E. Baldwin, R. M. Adlington, D. Bebbington, A. T. Russell, Tetrahedron 1994, 50, 12015-12028, and references cited therein.
19. Reviews: [10a] A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Top. Curr. Chem. 1999, 207, 89-147.
20. [10b] A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Zh. Org. Khim. 1996, 32, 1607-1626; Russ. J. Org. Chem. (Engl. Transl.) 1996, 32, 1555-1575.
21. [10b] A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Zh. Org. Khim. 1996, 32, 1607-1626; Russ. J. Org. Chem. (Engl. Transl.) 1996, 32, 1555-1575.
22. A. de Meijere, S. I. Kozhushkov, N. S. Zefirov, Synthesis 1993, 681-683.
23. V. N. Belov, A. de Meijere, unpublished results.
24. K. Miyazawa, S. Löhr, A. de Meijere, Mol. Cryst. Liq. Cryst., submitted.
25. [14a] A. J. Birch, J. Chem. Soc. 1944, 430-436.
26. [14b] R. A. Benkeser, G. Schroll, D. M. Sauvre, J. Am. Chem. Soc. 1955, 77, 3378-3379.
27. M. von Seebach, forthcoming Dissertation, Universität Göttingen.
28. This indicates the enhanced reactivity of bicyclopropylidene (5) and its derivatives in comparison with unstrained tetrasubstituted alkenes under Birch and Benkeser reduction conditions: [16a] E. E. Kaiser, Synthesis 1972, 391-415.
29. [16b] A. J. Birch, H. Williamson, Org. React. 1976, 24, 1-65.
30. [16c] M. von Seebach, Diplomarbeit, Universität Göttingen, 1997.
31. The N-isopropyl amides 12c-e were prepared for better bio-availability. The potential biological activities of these compounds are being tested in the laboratories of the Bayer company.
32. The amides 12 were prepared from the acids 11, adapting published procedures: [18a] L. W. L. Woo, H. J. Smith, K. J. Barrell, P. J. Nicholls, J. Chem. Soc., Perkin Trans. 1 1993, 2549-2554.
33. [18b] A. Vasella, R. Voeffrau, J. Pless, R. Huguenin, Helv. Chim. Acta 1983, 66, 1241-1252.
34. H. Schlegel, K. Schmidt, Allgemeine Mikrobiologie, 6th ed., Thieme, Stuttgart, 1985, p. 422-423.
35. J. A. Landgrebe, L. W. Becker, J. Org. Chem. 1968, 33, 1173-1178.
36. T. Heiner, S. I. Kozhushkov, M. Noltemeyer, T. Haumann, R. Boese, A. de Meijere, Tetrahedron 1996, 52, 12185 - 12196.
37. Test organisms: Pseudomonas sp. IR1, Pseudomonas sp. IR1 A1, Acinetobacter sp. BD413, Rhodococcus erythropolis BD2, Rhodococcus erythropolis CW25, Nocardia contina B276, Rhodococcus rhodocrous P-3-28, Rhodococcus rhodocrous P-3-101-1, Rhodococcus ruber P-IV-B-11, Rhodococcus ruber P-V-B-171, Rhodococcus fasciens B-2-2, Mycobacterium sp. E-2-1, Rhodococcus fasciens B-3-36-3, Rhodococcus rhodochrous P-II-123-1, Rhodococcus fasciens B-2-25, Mycobacterium sp. E-2-47, Mycobacterium sp. E-1-35, Mycobacterium sp. E-1-57, Rhodococcus rhodocrous ATCC 12674, Rhodococcus rhodocrous ATCC 4277.
38. H. Saeki, Dissertation, Universität Göttingen 1998.
39. The iodides 6b and 6f were prepared adapting published procedures: [24a] K. Mori, Tetrahedron 1974, 30, 3817-3820.
40. [24b] K. Mori, H. Watanabe, K. Yanagi, M. Minobe, Tetrahedron 1985, 41, 3663-3672.
41. K. Mori, T. Sakai, H. Hamamoto, Agric. Biol. Chem. 1986, 50, 1621-1628.
42. K. J. Shea, L. D. Burke, J. Org. Chem. 1988, 53, 318-327.
43. G. Lease, K. J. Shea, J. Am. Chem. Soc. 1993, 115, 2248-2260.
44. D. Savoia, C. Trombini, A. Umani-Ronchi, J. Org. Chem. 1982, 47, 564-566.
45. B. Dabrock, J. Riedel, J. Bertram, G. Gottschalk, Arch. Microbiol. 1992, 158, 9-13.
46. B. Dabrock, M. Keßeler, B. Averhoff, G. Gottschalk, Appl. Environ. Microbiol. 1992, 60, 853-860.