The Isoxazoline Route to the Molecules of Nature

Accounts of Chemical Research

Volumn 17, Issue 12, 1984, Pages 410-416

  Kozikowski, Alan P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041112261     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar00108a001     Document Type: Article

References (51)

1. C. Grundmann and P. Grünanger, “The Nitrile Oxides”, Springer-Verlag, New York (1971).
2. A. P. Kozikowski in “Comprehensive Heterocyclic Chemistry”, A. R. Katritzky, Ed., Pergamon Press, Oxford (1984).
3. C. Weygand and E. Bauer, Justus Liebigs Ann. Chem., 459, 123 (1927).
4. A. Quilico and G. Speroni, Gazz. Chem. Hal, 76, 148 (1946).
5. R. Huisgen, Proc. Chem. Soc. 357 (1961).
6. For a thorough discussion of regioselectivity in nitrile oxide cycloaddition reactions, see: K. N. Houk, Acc. Chem. Res., 8, 361 (1975).
7. N. K. Kochetokov and S. D. Sokolov, Adv. Heterocycl. Chem., 2, 365 (1963);
8. B. J. Wakefield and D. J. Wright, Adv. Heterocycl. Chem., 25, 147 (1979).
9. More recently the isoxazole ring has also been used to gain access to β-hydroxy ketones. See, for example: P. G. Baraldi, A. Barco, S. Benetti, F. Moroder, G. P. Pollini, and D. Simoni, J. Org. Chem., 48, 1297 (1983) and references therein.
10. G. Stork, M. Ohashi, H. Kamachi, and H. Kakisawa, J. Org. Chem., 36, 2784 (1971).
11. V. Jäger and H. Grund, Angew. Chem. Int. Ed. Engl., 15, 50 (1976).
12. V. Jäger and W. Schwab, Tetrahedron Lett., 3129 (1978);
13. V. Jäger, V. Buss, and W. Schwab, Tetrahedron Lett., 3133 (1978).
14. V. Jäger and V. Buss, Liebigs Ann. Chem., 101 (1980);
15. V. Jäger, V. Buss, and W. Schwab, Liebigs Ann. Chem., 122 (1980).
16. A. P. Kozikowski and H. Ishida, J. Am. Chem. Soc. 102, 4265 (1980).
17. A. P. Kozikowski and Y. Y. Chen, J. Org. Chem., 46, 5248 (1981).
18. K. F. Burri, R. A. Cardone, W. Y. Chen, and P. Rosen, J. Am. Chem. Soc. 100, 7069 (1978).
19. For an elegant application of the type a transformation to biotin, see: P. N. Confalone, E. D. Lollar, G. Pizzolato, and M. R. Uskokovic, J. Am. Chem. Soc. 100, 6291 (1978).
20. R. H. Wollengerg and J. E. Goldstein, Synthesis, 757 (1980).
21. A. P. Kozikowski and M. Adamczyk, Tetrahedron Lett., 23, 3123 (1982).
22. P. S. Bailey, “Ozonation in Organic Chemistry”, Vol. II, Academic Press, New York (1982).
23. The cleavage of isoxazolines to β-hydroxy ketones by Ti3+ has also been reported: S. H. Andersen, N. B. Das, R. D. Jorgensen, G. Kjeldsen, J. S. Knudsen, S. C. Sharma, and K. B. G. Torssell, Acta Chem. Scand., Ser. B, B36, 1 (1982);
24. S. K. Mukerji, K. K. Sharma, and K. B. G. Torssell, Tetrahedron, 39, 2231 (1983);
25. S. H. Andersen, K. K. Sharma and K. B. G. Torssell, Tetrahedron, 39, 2241 (1983).
26. For an important study on the use of boric acid in isoxazoline hydrogenations, see D. P. Curran, J. Am. Chem. Soc. 105, 5826 (1983).
27. BF3.OEt2 as an additive: S. F. Martin and B. Dupre, Tetrahedron Lett., 24, 1337 (1983).
28. A. P. Kozikowski and P. D. Stein, J. Am. Chem. Soc. 104, 4023 (1982).
29. T. Hoshino and M. Mukaiyama, J. Am. Chem. Soc., 82, 5339 (1960).
30. A. P. Kozikowski and P. D. Stein, J. Org. Chem., 49, 2301 (1984).
31. G. Stork and M. Isobe, J. Am. Chem. Soc. 97, 4745, 6260 (1975).
32. A. P. Kozikowski and Y. Y. Chen, Tetrahedron Lett., 23, 2081 (1982).
33. S. Goldstein, unpublished results from the University of Pittsburgh.
34. C. S. Li, unpublished results.
35. A. P. Kozikowski and B. Mugrage, Tetrahedron Lett., 24, 3705 (1983).
36. For the preparation of 9-, 13-, 15-, and 16-membered lactones by the INOC reaction, see: M. Asaoka, M. Abe, T. Mukuta, and H. Takei, Chem. Lett., 215 (1982).
37. A. P. Kozikowski and P.-U. Park, J. Org. Chem., 49, 1674 (1984).
38. A. P. Kozikowski and P.-W. Yen, Tetrahedron. Lett., submitted for publication.
39. A. P. Kozikowski and J. G. Scripko, J. Am. Chem. Soc. 106, 353 (1984).
40. A. P. Kozikowski, K. Hiraga, J. P. Springer, B. C. Wang, and Z.-B. Xu, J. Am. Chem. Soc. 106, 1845 (1984).
41. A. P. Kozikowski and M. Adamczyk, J. Org. Chem., 48, 366 (1983).
42. G. Zinner and H. Gunther, Chem. Ber., 98, 1353 (1965).
43. A. P. Kozikowski and A. K. Ghosh, Tetrahedron Lett., 24, 2623 (1983).
44. A. P. Kozikowski and S. Goldstein, J. Org. Chem., 48, 1139 (1983).
45. A. P. Kozikowski, Y. Kitagawa, and J. P. Springer, J. Chem. Soc. Chem. Commun., 1460 (1983).
46. A. P. Kozikowski and A. K. Ghosh, J. Am. Chem. Soc. 104, 5788 (1982).
47. C. H. Heathcock, S. D. Young, J. P. Hagen, M. C. Pirrung, C. T. White, and D. J. VanDerveer, J. Org. Chem., 45, 3846 (1980). For other comparisons, see ref 32.
48. Reasonable levels of diastereoselection are also observed with the tert-butyldimethylsilyl ether of 3-buten-2-ol. A. P. Kozikowski and A. K. Ghosh, J. Org. Chem., 49, 2762 (1984).
49. A. P. Kozikowski and C. S. Li, J. Org. Chem., in press.
50. S. Danishefsky, J. F. Kerwin, and S. Kobayashi, J. Am. Chem. Soc. 104, 358 (1982).
51. Due to space limitations I could not adequately cover the important work of other investigators. To them I apologize in advance. Attention is called to ref 2 and to a recent article [V. Jäger and R. Schohe, Tetrahedron, 40, 2199 (1984)] for more detailed referencing in the nitrile oxide cycloaddition area.