Oxazolium-derived azomethine ylides. External oxazole activation and internal dipole trapping in the synthesis of an aziridinomitosene

Journal of Organic Chemistry

Volumn 65, Issue 18, 2000, Pages 5498-5505

  Vedejs, Edwin ^a,b   Piotrowski, David W ^a   Tucci, Fabio C ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; AZIRIDINOMITOSENE; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

AZIRIDINES; MAGNETIC RESONANCE SPECTROSCOPY; OXAZOLES; SPECTROPHOTOMETRY, INFRARED;

EID: 0033835583     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0001277     Document Type: Article

References (41)

1. (a) Vedejs, E.; Grissom, J. W. J. Am. Chem. Soc. 1988, 110, 3238.
2. (b) Vedejs, E.; Dax, S. L. Tetrahedron Lett. 1989, 30, 2627.
3. Vedejs, E.; Piotrowski, D. W. J. Org. Chem. 1993, 58, 1341.
4. Vedejs, E.; Monahan, S. D. J. Org. Chem. 1997, 62, 4763.
5. Lown, J. W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Chapter 6.
6. Hassner, A.; Fischer, B. Tetrahedron Lett. 1990, 31, 7213. Hassner, A.; Fischer, B. J. Org. Chem. 1992, 57, 3070.
7. Hassner, A.; Fischer, B. Tetrahedron Lett. 1990, 31, 7213. Hassner, A.; Fischer, B. J. Org. Chem. 1992, 57, 3070.
8. (a) Patrick, J. B.; Williams, R. P.; Meyer, W. E.; Fulmor, W.; Cosulich, D. B.; Broschard, R. W.; Webb, J. S. J. Am. Chem. Soc. 1964, 86, 1889.
9. (b) Reviews: Remers, W. A. In The Chemistry of Antitumor Antibiotics; Wiley: New York, 1979; Vol. 1, pp 221-276. Tisler, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: New York, 1988; Vol. 45, pp 38-150. Tomasz, M. Chem. Biol. 1995, 2, 575.
10. (b) Reviews: Remers, W. A. In The Chemistry of Antitumor Antibiotics; Wiley: New York, 1979; Vol. 1, pp 221-276. Tisler, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: New York, 1988; Vol. 45, pp 38-150. Tomasz, M. Chem. Biol. 1995, 2, 575.
11. (b) Reviews: Remers, W. A. In The Chemistry of Antitumor Antibiotics; Wiley: New York, 1979; Vol. 1, pp 221-276. Tisler, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: New York, 1988; Vol. 45, pp 38-150. Tomasz, M. Chem. Biol. 1995, 2, 575.
12. Dong, W.; Jimenez, L. S. J. Org. Chem. 1999, 64, 2520.
13. (a) Review: Danishefsky, S. J.; Schkeryantz, J. M. Synlett 1995, 475.
14. (b) Shaw, K. J.; Luly, J. R.; Rapoport, H. J. Org. Chem. 1985, 50, 4515.
15. (c) Lee, S.; Lee, W. M.; Sulikowski, G. A. J. Org. Chem. 1999, 64, 4224. Edstrom, E. D.; Yu, T. Tetrahedron 1997, 53, 4549. Wang, Z.; Jimenez, L. S. J. Org. Chem. 1996, 61, 816. Danishefsky, S. J.; Egbertson, M. J. Am. Chem. Soc. 1986, 108, 4648. Iyenger, B. S.; Remers, W. A.; Bradner, W. T. J. Med. Chem. 1986, 29, 1864. Cory, R. M.; Ritchie, B. M. J. Chem. Soc., Chem. Commun. 1983, 1244. Suita, G. J.; Franck, R. W.; Kempton, R. J. J. Org. Chem. 1974, 39, 3739. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 19. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 4107.
16. (c) Lee, S.; Lee, W. M.; Sulikowski, G. A. J. Org. Chem. 1999, 64, 4224. Edstrom, E. D.; Yu, T. Tetrahedron 1997, 53, 4549. Wang, Z.; Jimenez, L. S. J. Org. Chem. 1996, 61, 816. Danishefsky, S. J.; Egbertson, M. J. Am. Chem. Soc. 1986, 108, 4648. Iyenger, B. S.; Remers, W. A.; Bradner, W. T. J. Med. Chem. 1986, 29, 1864. Cory, R. M.; Ritchie, B. M. J. Chem. Soc., Chem. Commun. 1983, 1244. Suita, G. J.; Franck, R. W.; Kempton, R. J. J. Org. Chem. 1974, 39, 3739. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 19. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 4107.
17. (c) Lee, S.; Lee, W. M.; Sulikowski, G. A. J. Org. Chem. 1999, 64, 4224. Edstrom, E. D.; Yu, T. Tetrahedron 1997, 53, 4549. Wang, Z.; Jimenez, L. S. J. Org. Chem. 1996, 61, 816. Danishefsky, S. J.; Egbertson, M. J. Am. Chem. Soc. 1986, 108, 4648. Iyenger, B. S.; Remers, W. A.; Bradner, W. T. J. Med. Chem. 1986, 29, 1864. Cory, R. M.; Ritchie, B. M. J. Chem. Soc., Chem. Commun. 1983, 1244. Suita, G. J.; Franck, R. W.; Kempton, R. J. J. Org. Chem. 1974, 39, 3739. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 19. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 4107.
18. (c) Lee, S.; Lee, W. M.; Sulikowski, G. A. J. Org. Chem. 1999, 64, 4224. Edstrom, E. D.; Yu, T. Tetrahedron 1997, 53, 4549. Wang, Z.; Jimenez, L. S. J. Org. Chem. 1996, 61, 816. Danishefsky, S. J.; Egbertson, M. J. Am. Chem. Soc. 1986, 108, 4648. Iyenger, B. S.; Remers, W. A.; Bradner, W. T. J. Med. Chem. 1986, 29, 1864. Cory, R. M.; Ritchie, B. M. J. Chem. Soc., Chem. Commun. 1983, 1244. Suita, G. J.; Franck, R. W.; Kempton, R. J. J. Org. Chem. 1974, 39, 3739. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 19. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 4107.
19. (c) Lee, S.; Lee, W. M.; Sulikowski, G. A. J. Org. Chem. 1999, 64, 4224. Edstrom, E. D.; Yu, T. Tetrahedron 1997, 53, 4549. Wang, Z.; Jimenez, L. S. J. Org. Chem. 1996, 61, 816. Danishefsky, S. J.; Egbertson, M. J. Am. Chem. Soc. 1986, 108, 4648. Iyenger, B. S.; Remers, W. A.; Bradner, W. T. J. Med. Chem. 1986, 29, 1864. Cory, R. M.; Ritchie, B. M. J. Chem. Soc., Chem. Commun. 1983, 1244. Suita, G. J.; Franck, R. W.; Kempton, R. J. J. Org. Chem. 1974, 39, 3739. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 19. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 4107.
20. (c) Lee, S.; Lee, W. M.; Sulikowski, G. A. J. Org. Chem. 1999, 64, 4224. Edstrom, E. D.; Yu, T. Tetrahedron 1997, 53, 4549. Wang, Z.; Jimenez, L. S. J. Org. Chem. 1996, 61, 816. Danishefsky, S. J.; Egbertson, M. J. Am. Chem. Soc. 1986, 108, 4648. Iyenger, B. S.; Remers, W. A.; Bradner, W. T. J. Med. Chem. 1986, 29, 1864. Cory, R. M.; Ritchie, B. M. J. Chem. Soc., Chem. Commun. 1983, 1244. Suita, G. J.; Franck, R. W.; Kempton, R. J. J. Org. Chem. 1974, 39, 3739. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 19. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 4107.
21. (c) Lee, S.; Lee, W. M.; Sulikowski, G. A. J. Org. Chem. 1999, 64, 4224. Edstrom, E. D.; Yu, T. Tetrahedron 1997, 53, 4549. Wang, Z.; Jimenez, L. S. J. Org. Chem. 1996, 61, 816. Danishefsky, S. J.; Egbertson, M. J. Am. Chem. Soc. 1986, 108, 4648. Iyenger, B. S.; Remers, W. A.; Bradner, W. T. J. Med. Chem. 1986, 29, 1864. Cory, R. M.; Ritchie, B. M. J. Chem. Soc., Chem. Commun. 1983, 1244. Suita, G. J.; Franck, R. W.; Kempton, R. J. J. Org. Chem. 1974, 39, 3739. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 19. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 4107.
22. (c) Lee, S.; Lee, W. M.; Sulikowski, G. A. J. Org. Chem. 1999, 64, 4224. Edstrom, E. D.; Yu, T. Tetrahedron 1997, 53, 4549. Wang, Z.; Jimenez, L. S. J. Org. Chem. 1996, 61, 816. Danishefsky, S. J.; Egbertson, M. J. Am. Chem. Soc. 1986, 108, 4648. Iyenger, B. S.; Remers, W. A.; Bradner, W. T. J. Med. Chem. 1986, 29, 1864. Cory, R. M.; Ritchie, B. M. J. Chem. Soc., Chem. Commun. 1983, 1244. Suita, G. J.; Franck, R. W.; Kempton, R. J. J. Org. Chem. 1974, 39, 3739. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 19. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 4107.
23. (c) Lee, S.; Lee, W. M.; Sulikowski, G. A. J. Org. Chem. 1999, 64, 4224. Edstrom, E. D.; Yu, T. Tetrahedron 1997, 53, 4549. Wang, Z.; Jimenez, L. S. J. Org. Chem. 1996, 61, 816. Danishefsky, S. J.; Egbertson, M. J. Am. Chem. Soc. 1986, 108, 4648. Iyenger, B. S.; Remers, W. A.; Bradner, W. T. J. Med. Chem. 1986, 29, 1864. Cory, R. M.; Ritchie, B. M. J. Chem. Soc., Chem. Commun. 1983, 1244. Suita, G. J.; Franck, R. W.; Kempton, R. J. J. Org. Chem. 1974, 39, 3739. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 19. Hirata, H.; Yamada, Y.; Matsui, M. Tetrahedron Lett. 1969, 4107.
24. Han, I.; Kohn, H. J. Org. Chem. 1991, 56, 4648.
25. (a) Wartski, L. J. Chem. Soc., Chem. Commun. 1977, 602.
26. (b) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121.
27. (a) Pridgen, L. N.; Shilcrat, S. C. Synthesis 1984, 1048.
28. (b) Quast, H.; von der Saal, W.; Stawitz, J. Angew. Chem. Int. Ed. Engl. 1981, 20, 588.
29. Oxazole 14 was prepared from i and acrylonitrile via ii and iii following methods described in ref 2 for the corresponding sequence from i and acetonitrile. (Formula Presented)
30. Alder, R. W. Chem. Rev. 1989, 89, 1215.
31. Gonzalez, C.; Greenhouse, R.; Tallabs, R.; Muchowski, J. Can. J. Chem. 1983, 61, 1697.
32. Balgobin, N.; Josephson, S.; Chattopadhyaya, J. B. Tetrahedron Lett. 1981, 22, 1915.
33. (a) The role of the N-benzyl group in the selective N-alkylation has been probed using analogues of 20 where Bn is replaced by H and OBz by iodide (see ref 16b for methodology to access the deprotected aziridines). Treatment of the NH aziridine with MeOTf in the presence of 2,6-di-tert-butyl-4-methylpyridine in deuterated aceonitrile gave ca. 25% of the N-methylaziridine as well as recovered starting material and decomposition products. Characteristic NMR shifts for oxazolium protons were also observed, indicating that the rates of oxazole and aziridine alkylation are similar in the absence of the N-benzyl substituent.
34. (b) Vedejs, E.; Klapars, A.; Naidu, B. N.; Piotrowski, D. W. Tucci, F. C. J. Am. Chem. Soc. 2000, 122, 5401.
35. For studies dealing with azomethine ylide approaches to mitosenes, see: Hershenson, F. M. J. Org. Chem. 1975, 40, 1260. Rebek, J.; Shabar, S. H.; Shue, Y.-K.; Gehret, J.-C.; Zimmerman, S. J. Org. Chem. 1984, 49, 5164. Rebek, J.; Shaber, S. H. Heterocycles 1981, 16, 1173. Rebek, J.; Gehret, J.-C. E. Tetrahedron Lett. 1977, 19, 3027. Anderson, W. K.; Corey, P. F. J. Org. Chem. 1977, 42, 559.
36. For studies dealing with azomethine ylide approaches to mitosenes, see: Hershenson, F. M. J. Org. Chem. 1975, 40, 1260. Rebek, J.; Shabar, S. H.; Shue, Y.-K.; Gehret, J.-C.; Zimmerman, S. J. Org. Chem. 1984, 49, 5164. Rebek, J.; Shaber, S. H. Heterocycles 1981, 16, 1173. Rebek, J.; Gehret, J.-C. E. Tetrahedron Lett. 1977, 19, 3027. Anderson, W. K.; Corey, P. F. J. Org. Chem. 1977, 42, 559.
37. For studies dealing with azomethine ylide approaches to mitosenes, see: Hershenson, F. M. J. Org. Chem. 1975, 40, 1260. Rebek, J.; Shabar, S. H.; Shue, Y.-K.; Gehret, J.-C.; Zimmerman, S. J. Org. Chem. 1984, 49, 5164. Rebek, J.; Shaber, S. H. Heterocycles 1981, 16, 1173. Rebek, J.; Gehret, J.-C. E. Tetrahedron Lett. 1977, 19, 3027. Anderson, W. K.; Corey, P. F. J. Org. Chem. 1977, 42, 559.
38. For studies dealing with azomethine ylide approaches to mitosenes, see: Hershenson, F. M. J. Org. Chem. 1975, 40, 1260. Rebek, J.; Shabar, S. H.; Shue, Y.-K.; Gehret, J.-C.; Zimmerman, S. J. Org. Chem. 1984, 49, 5164. Rebek, J.; Shaber, S. H. Heterocycles 1981, 16, 1173. Rebek, J.; Gehret, J.-C. E. Tetrahedron Lett. 1977, 19, 3027. Anderson, W. K.; Corey, P. F. J. Org. Chem. 1977, 42, 559.
39. For studies dealing with azomethine ylide approaches to mitosenes, see: Hershenson, F. M. J. Org. Chem. 1975, 40, 1260. Rebek, J.; Shabar, S. H.; Shue, Y.-K.; Gehret, J.-C.; Zimmerman, S. J. Org. Chem. 1984, 49, 5164. Rebek, J.; Shaber, S. H. Heterocycles 1981, 16, 1173. Rebek, J.; Gehret, J.-C. E. Tetrahedron Lett. 1977, 19, 3027. Anderson, W. K.; Corey, P. F. J. Org. Chem. 1977, 42, 559.
40. Hartung, W. H.; Simonoff, R. Org. React. 1953, 7, 263.
41. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156.