Synthesis of the polycyclopropane antibiotic FR-900848 via the Horeau gambit

Journal of the American Chemical Society

Volumn 118, Issue 25, 1996, Pages 6096-6097

  Falck, J R ^a   Mekonnen, Belew ^a   Yu, Jurong ^a   Lai, Jing Yu ^a  

^a UNIVERSITY OF TEXAS AT DALLAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; FR 900848; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030038686     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961093g     Document Type: Article

References (39)

1. Yoshida, M.; Ezaki, M.; Hashimoto, M.; Yamashita, M.; Shigematsu, N.; Okuhara, M.; Kohsaka, M.; Horikoshi, K. J Antibiotics 1990, 43, 748-754.
2. Sternberg, S. Science 1994, 266, 1632-1634. Georgopapadakou, N. H.; Walsh, T. J. Ibid. 1994, 264, 371-373.
3. Sternberg, S. Science 1994, 266, 1632-1634. Georgopapadakou, N. H.; Walsh, T. J. Ibid. 1994, 264, 371-373.
4. Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1994, 35, 9181-9184. Armstrong, R. W.; Maurer, K. W. Ibid. 1995, 36, 357-360. Barrett, A. G. M.; Kasdorf, K.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1781-1782. Barrett, A. G. M.; Doubleday, W. W.; Tustin, G. J.; White, A. J. P.; Williams, D. J. Ibid. 1994, 1783-1784. Barrett, A. G. M.; Tustin, G. J. Ibid. 1995, 355-356. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A.J. P.; Williams, D. J. Ibid. 1995, 407-408. Barrett, A. G. M.; Kasdorf, K.; White, A. J. P.; Williams, D. J. Ibid. 1995, 649-650. Barrett, A. G. M.; Kasdorf, K.; Tustin, G. J.; Williams, D. J. Ibid. 1995, 1143-1144.
5. Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1994, 35, 9181-9184. Armstrong, R. W.; Maurer, K. W. Ibid. 1995, 36, 357-360. Barrett, A. G. M.; Kasdorf, K.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1781-1782. Barrett, A. G. M.; Doubleday, W. W.; Tustin, G. J.; White, A. J. P.; Williams, D. J. Ibid. 1994, 1783-1784. Barrett, A. G. M.; Tustin, G. J. Ibid. 1995, 355-356. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A.J. P.; Williams, D. J. Ibid. 1995, 407-408. Barrett, A. G. M.; Kasdorf, K.; White, A. J. P.; Williams, D. J. Ibid. 1995, 649-650. Barrett, A. G. M.; Kasdorf, K.; Tustin, G. J.; Williams, D. J. Ibid. 1995, 1143-1144.
6. Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1994, 35, 9181-9184. Armstrong, R. W.; Maurer, K. W. Ibid. 1995, 36, 357-360. Barrett, A. G. M.; Kasdorf, K.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1781-1782. Barrett, A. G. M.; Doubleday, W. W.; Tustin, G. J.; White, A. J. P.; Williams, D. J. Ibid. 1994, 1783-1784. Barrett, A. G. M.; Tustin, G. J. Ibid. 1995, 355-356. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A.J. P.; Williams, D. J. Ibid. 1995, 407-408. Barrett, A. G. M.; Kasdorf, K.; White, A. J. P.; Williams, D. J. Ibid. 1995, 649-650. Barrett, A. G. M.; Kasdorf, K.; Tustin, G. J.; Williams, D. J. Ibid. 1995, 1143-1144.
7. Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1994, 35, 9181-9184. Armstrong, R. W.; Maurer, K. W. Ibid. 1995, 36, 357-360. Barrett, A. G. M.; Kasdorf, K.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1781-1782. Barrett, A. G. M.; Doubleday, W. W.; Tustin, G. J.; White, A. J. P.; Williams, D. J. Ibid. 1994, 1783-1784. Barrett, A. G. M.; Tustin, G. J. Ibid. 1995, 355-356. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A.J. P.; Williams, D. J. Ibid. 1995, 407-408. Barrett, A. G. M.; Kasdorf, K.; White, A. J. P.; Williams, D. J. Ibid. 1995, 649-650. Barrett, A. G. M.; Kasdorf, K.; Tustin, G. J.; Williams, D. J. Ibid. 1995, 1143-1144.
8. Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1994, 35, 9181-9184. Armstrong, R. W.; Maurer, K. W. Ibid. 1995, 36, 357-360. Barrett, A. G. M.; Kasdorf, K.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1781-1782. Barrett, A. G. M.; Doubleday, W. W.; Tustin, G. J.; White, A. J. P.; Williams, D. J. Ibid. 1994, 1783-1784. Barrett, A. G. M.; Tustin, G. J. Ibid. 1995, 355-356. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A.J. P.; Williams, D. J. Ibid. 1995, 407-408. Barrett, A. G. M.; Kasdorf, K.; White, A. J. P.; Williams, D. J. Ibid. 1995, 649-650. Barrett, A. G. M.; Kasdorf, K.; Tustin, G. J.; Williams, D. J. Ibid. 1995, 1143-1144.
9. Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1994, 35, 9181-9184. Armstrong, R. W.; Maurer, K. W. Ibid. 1995, 36, 357-360. Barrett, A. G. M.; Kasdorf, K.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1781-1782. Barrett, A. G. M.; Doubleday, W. W.; Tustin, G. J.; White, A. J. P.; Williams, D. J. Ibid. 1994, 1783-1784. Barrett, A. G. M.; Tustin, G. J. Ibid. 1995, 355-356. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A.J. P.; Williams, D. J. Ibid. 1995, 407-408. Barrett, A. G. M.; Kasdorf, K.; White, A. J. P.; Williams, D. J. Ibid. 1995, 649-650. Barrett, A. G. M.; Kasdorf, K.; Tustin, G. J.; Williams, D. J. Ibid. 1995, 1143-1144.
10. Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1994, 35, 9181-9184. Armstrong, R. W.; Maurer, K. W. Ibid. 1995, 36, 357-360. Barrett, A. G. M.; Kasdorf, K.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1781-1782. Barrett, A. G. M.; Doubleday, W. W.; Tustin, G. J.; White, A. J. P.; Williams, D. J. Ibid. 1994, 1783-1784. Barrett, A. G. M.; Tustin, G. J. Ibid. 1995, 355-356. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A.J. P.; Williams, D. J. Ibid. 1995, 407-408. Barrett, A. G. M.; Kasdorf, K.; White, A. J. P.; Williams, D. J. Ibid. 1995, 649-650. Barrett, A. G. M.; Kasdorf, K.; Tustin, G. J.; Williams, D. J. Ibid. 1995, 1143-1144.
11. Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1994, 35, 9181-9184. Armstrong, R. W.; Maurer, K. W. Ibid. 1995, 36, 357-360. Barrett, A. G. M.; Kasdorf, K.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1781-1782. Barrett, A. G. M.; Doubleday, W. W.; Tustin, G. J.; White, A. J. P.; Williams, D. J. Ibid. 1994, 1783-1784. Barrett, A. G. M.; Tustin, G. J. Ibid. 1995, 355-356. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A.J. P.; Williams, D. J. Ibid. 1995, 407-408. Barrett, A. G. M.; Kasdorf, K.; White, A. J. P.; Williams, D. J. Ibid. 1995, 649-650. Barrett, A. G. M.; Kasdorf, K.; Tustin, G. J.; Williams, D. J. Ibid. 1995, 1143-1144.
12. Barrett, A. G. M.; Kasdorf, K. Chem. Commun. 1996, 325-326.
13. Examples of polycyclopropane syntheses: Conia, J. M.; Denis, J. M. Tetrahedron Lett. 1969, 3545-3546. Ripoll, J. L.; Limasset, J. C.; Conia, J. M. Tetrahedron 1971, 27, 2431-2452. Kostikov, R. R.; Molchanov, A. P. Zh. Org. Khim. 1978, 14, 1108-1109. de Meijere, A.; Jaekel, F.; Simon, A.; Borrmann, H.; Kohler, J.; Johnels, D.; Scott, L. T. J. Am. Chem. Soc. 1991, 113, 3935-3941.
14. Examples of polycyclopropane syntheses: Conia, J. M.; Denis, J. M. Tetrahedron Lett. 1969, 3545-3546. Ripoll, J. L.; Limasset, J. C.; Conia, J. M. Tetrahedron 1971, 27, 2431-2452. Kostikov, R. R.; Molchanov, A. P. Zh. Org. Khim. 1978, 14, 1108-1109. de Meijere, A.; Jaekel, F.; Simon, A.; Borrmann, H.; Kohler, J.; Johnels, D.; Scott, L. T. J. Am. Chem. Soc. 1991, 113, 3935-3941.
15. Examples of polycyclopropane syntheses: Conia, J. M.; Denis, J. M. Tetrahedron Lett. 1969, 3545-3546. Ripoll, J. L.; Limasset, J. C.; Conia, J. M. Tetrahedron 1971, 27, 2431-2452. Kostikov, R. R.; Molchanov, A. P. Zh. Org. Khim. 1978, 14, 1108-1109. de Meijere, A.; Jaekel, F.; Simon, A.; Borrmann, H.; Kohler, J.; Johnels, D.; Scott, L. T. J. Am. Chem. Soc. 1991, 113, 3935-3941.
16. Examples of polycyclopropane syntheses: Conia, J. M.; Denis, J. M. Tetrahedron Lett. 1969, 3545-3546. Ripoll, J. L.; Limasset, J. C.; Conia, J. M. Tetrahedron 1971, 27, 2431-2452. Kostikov, R. R.; Molchanov, A. P. Zh. Org. Khim. 1978, 14, 1108-1109. de Meijere, A.; Jaekel, F.; Simon, A.; Borrmann, H.; Kohler, J.; Johnels, D.; Scott, L. T. J. Am. Chem. Soc. 1991, 113, 3935-3941.
17. For a thorough discussion of the Horeau amplification principle, see: Rautenstrauch, V. Bull. Soc. Chim. Fr. 1994, 131, 515-524.
18. 18-polyunsaturated fatty acid and that the cyclopropanes arise from the addition of one-carbon units donated by S-adenosylmethionine or its equivalent. Since the thermodynamically most stable form of this hypothetical precursor is all-trans, then the cyclopropanes and olefins in 2 would also be trans. equation presentated
19. Available from Aldrich Chem. Co.
20. Dr. Hirokazu Tanaka (Fujisawa Pharmaceutical Co., Ltd.), personal communication.
21. Dimerizations of cyclopropane anions have precedence: Slabey, V. A. J. Am. Chem. Soc. 1952, 74, 4928-4930. Kai, Y.; Knochel, P.; Kwiatkowski, S.; Dunitz, J. D.; Oth, J. F. M.; Seebach, D. Helv. Chim. Acta 1982, 65, 137-161. O'Bannon, P. E.; Dailey, W. P. J. Am. Chem. Soc. 1989, 111, 9244-9245.
22. Dimerizations of cyclopropane anions have precedence: Slabey, V. A. J. Am. Chem. Soc. 1952, 74, 4928-4930. Kai, Y.; Knochel, P.; Kwiatkowski, S.; Dunitz, J. D.; Oth, J. F. M.; Seebach, D. Helv. Chim. Acta 1982, 65, 137-161. O'Bannon, P. E.; Dailey, W. P. J. Am. Chem. Soc. 1989, 111, 9244-9245.
23. Dimerizations of cyclopropane anions have precedence: Slabey, V. A. J. Am. Chem. Soc. 1952, 74, 4928-4930. Kai, Y.; Knochel, P.; Kwiatkowski, S.; Dunitz, J. D.; Oth, J. F. M.; Seebach, D. Helv. Chim. Acta 1982, 65, 137-161. O'Bannon, P. E.; Dailey, W. P. J. Am. Chem. Soc. 1989, 111, 9244-9245.
24. n units/dimerization) inherent in this strategy allows one to rapidly accrue repeating functionality. This would be especially important for the preparation of higher homologs of 1 containing, for example, eight serial cyclopropanes.
25. Review: Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197-1207.
26. Imai, N.; Sakamoto, K.; Takahashi, H.; Kobayashi, S. Tetrahedron Lett. 1994, 35, 7045-7048. Jung, M. E.; Light, L, A. Ibid. 1982, 23, 3851-3854.
27. Imai, N.; Sakamoto, K.; Takahashi, H.; Kobayashi, S. Tetrahedron Lett. 1994, 35, 7045-7048. Jung, M. E.; Light, L, A. Ibid. 1982, 23, 3851-3854.
28. 13C NMR and MS analysis. The elemental composition of an analytical sample was confirmed by combustion analysis or high-resolution mass spectroscopy.
29. Whitesides, G. M.; Casey, C. P.; Krieger, J. K. J Am. Chem. Soc. 1971, 93, 1379-1389.
30. Lipshutz, B. H.; Kayser, F.; Maullin, N. Tetrahedron Lett. 1994, 35, 815-818.
31. cf.: Walborsky, H. M.; Banks, R. B.; Banks, M. L. A.; Duraisamy, M. Organometallics 1982, 1, 667-674.
32. t ≈ 29 min.
33. Barton, D. H. R.; Crich, D. C.; Motherwell, W. B. Tetrahedron Lett. 1983, 24, 4979-4982.
34. A better indication of the stereospecificity is seen in the dimerization of the cis-analog of 11. The all-syn-trans,cis,cis,trans-tetracyclopropane dimer was isolated in 80% yield, and no other stereoisomers were observed.
35. t ≈ 17.6 min.
36. Hughes, D. L. Org. React. 1992, 42, 335-656.
37. Kocienski, P. Phosphorus Sulfur 1985, 24, 97-127.
38. Prepared from commercial uridine by a conventional sequence as summarized below. equation presentated
39. 6) of synthetic and natural FR-900848 observed by Dr. Krista Kasdorf, in the laboratories of Professor A. G. M. Barrett, is of a magnitude comparable to ours (Prof. A. G. M. Barrett, personal communication).