Microwave-assisted rearrangement of vinylaziridines to 3-pyrrolines: Formal synthesis of (-)-anisomycin

Synlett

Volumn , Issue 20, 2005, Pages 3099-3102

  Hirner, Sebastian ^a   Somfai, Peter ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Pyrrolines; Rearrangement; Ring expansion; Total synthesis; Vinylaziridines

Indexed keywords

ANISOMYCIN; ANTIBIOTIC AGENT; AZIRIDINE DERIVATIVE; PYRROLINE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLAZIRIDINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMER; MICROWAVE RADIATION; REACTION ANALYSIS; SYNTHESIS; THERMODYNAMICS;

EID: 29744467990     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-921934     Document Type: Article

References (46)

1. For recent examples of 3-pyrrolines as intermediates in organic synthesis, see: (a) Green, M. P.; Prodger, J. C.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6609.
2. (b) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621.
3. (c) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
4. (d) As MAO inhibitors, see: Lee, Y.; Huang, H.; Sayre, L. M. J. Am. Chem. Soc. 1996, 118, 7241.
5. (e) As NMDA receptor agonists, see: Rondeau, D.; Gill, P.; Chan, M.; Curry, K.; Lubell, W. D. Bioorg. Med. Chem. Lett. 2000, 10, 771.
6. (f) As κ-agonists, see: Mou, Q.-Y.; Chen, J.; Zhu, Y.-C.; Zhou, D.-H.; Chi, Z.-Q.; Long, Y.-Q. Bioorg. Med. Chem. Lett. 2002, 12, 2287.
7. (g) As tumor inhibitors, see: Anderson, W. K.; Milowsky, A. S. J. Med. Chem. 1987, 30, 2144.
8. For recent examples, see: (a) Dieter, R. K.; Chen, N.; Yu, H.; Nice, L. E.; Gore, V. K. J. Org. Chem. 2005, 70, 2109.
9. (b) Morita, N.; Krause, N. Org. Lett. 2004, 6, 4121.
10. (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855.
11. (d) Green, M. P.; Prodger, J. C.; Sherlock, A. E.; Hayes, C. J. Org. Lett. 2001, 3, 3377.
12. (a) Atkinson, R. S.; Rees, C. W. J. Chem. Soc. C 1969, 778.
13. (b) Scheiner, P. J. Org. Chem. 1967, 32, 2628.
14. (c) Fugami, K.; Miura, K.; Morizawa, Y.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron 1989, 45, 3089.
15. For reviews, see: (d) Somfai, P.; Åhman, J. In Targets In Heterocyclic Systems; Italian Society of Chemistry: Rome, 1999, 341.
16. (e) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, 899.
17. For a definition of the term-activated aziridine, see: Ham, G. E. J. Org. Chem. 1964, 29, 3052.
18. 10b
19. HH coupling constant of the ring protons (cis ca. 6.8-8.4 Hz; trans ca. 4.1-4.4 Hz).
20. A similar isomerization of vinylaziridines, catalyzed by Pd(0), has been published: (a) Mimura, N.; Ibuka, T.; Akaji, M.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Chem. Commun. 1996, 351.
21. (b) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999.
22. For ab initio calculations of the energy difference between different conformations of vinylaziridines, see: Toda, A.; Aoyama, H.; Mimura, N.; Ohno, H.; Fujii, N.; Ibuka, T. J. Org. Chem. 1998, 63, 7053.
23. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
24. (a) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250.
25. (b) Lindström, U. M.; Olofsson, B.; Somfai, P. Tetrahedron Lett. 1999, 40, 9273.
26. The microwave heating was performed with a Smith Creator single mode cavity from Personal Chemistry AB, Uppsala, Sweden, equipped with a magnetic stirrer and automatic temperature control.
27. +. The analytical data of compounds 2b and 2g were in accordance to literature data. See: Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929.
28. (a) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589.
29. (b) Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Chen, M.-B. J. Org. Chem. 1996, 61, 4641.
30. (a) Sobin, B. A.; Tanner, F. W. Jr. J. Am. Chem. Soc. 1954, 76, 4053.
31. (b) The Merck Index, 12th ed.; Windholz, M., Ed.; Merck: Whitehouse Station, NJ, 1996, 710.
32. (c) Hosoya, Y.; Kameyama, T.; Naganawa, H.; Okami, Y.; Takeuchi, T. J. Antibiot. 1993, 46, 1300.
33. (d) Nader, K.; Schafe, G. E.; Le Doux, J. E. Nature (London) 2000, 406, 722.
34. For examples, see: (a) Kaden, S.; Brockmann, M.; Reissig, H. U. Helv. Chim. Acta 2005, 88, 1826.
35. (b) Kim, J. H.; Curtis-Long, M. J.; Seo, W. D.; Ryu, Y. B.; Yang, M. S.; Park, K. H. J. Org. Chem. 2005, 70, 4082.
36. (c) Takahata, H.; Banba, Y.; Tajima, M.; Momose, T. J. Org. Chem. 1991, 56, 240.
37. (d) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861.
38. (e) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419.
39. (f) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113.
40. (g) Buchanan, J. G.; MacLean, K. A.; Wightman, R. H.; Paulsen, H. J. Chem. Soc., Perkin Trans. 1 1985, 1463.
41. (h) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076.
42. (a) Hu, S.; Jayaraman, S.; Oehlschlager, A. C. J. Org. Chem. 1996, 61, 7513.
43. (b) Hertweck, C.; Boland, W. J. Org. Chem. 1999, 64, 4462.
44. 16b The ee was shown to be >95% by chiral HPLC analysis (Chiracel OD, hexane-i-PrOH, 99.5:0.5, 0.5 mL/min).
45. 15e}.
46. 2).