A novel short approach to (Z)-pulchellalactam through transition-metal- catalyzed atom-transfer radical cyclization of 1-isopropylprop-2-enyl dichloroacetate

Synthesis

Volumn , Issue 12, 2007, Pages 1882-1886

  Felluga, Fulvia ^a   Ghelfi, Franco ^b   Pagnoni, Ugo M ^b   Parsons, Andrew F ^c   Pattarozzi, Mariella ^d   Roncaglia, Fabrizio ^b   Valentin, Ennio ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

^b UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^c UNIVERSITY OF YORK   (United Kingdom)

^d UNIVERSITY OF PADOVA   (Italy)

Author keywords

Cyclizations; Eliminations; Lactams; Lactones; Radical reactions

Indexed keywords

DEHYDROCHLORINATION; DICHLOROLACTONE; PROTOTROPIC REARRANGEMENT;

ATOM TRANSFER RADICAL POLYMERIZATION; CATALYSIS; CYCLIZATION; TRANSITION METAL ALLOYS;

ENZYME INHIBITION;

1 ISOPROPYLPROP 2 ENYLDICHOLOACETATE; ACETIC ACID DERIVATIVE; ENZYME INHIBITOR; PULCHELLALACTAM; UNCLASSIFIED DRUG;

ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; CATALYSIS; CHLORINATION; CYCLIZATION; RADICAL REACTION;

EID: 34347405320     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983709     Document Type: Article

References (39)

1. (a) Bialy, L.; Waldmann, H. Angew. Chem. Int. Ed. 2005, 44, 3814.
2. (b) Dewang, P. M.; Hsu, N.-M.; Peng, S.-Z.; Li, W.-R. Curr. Med. Chem. 2005, 12, 1.
3. (a) Hooft van Huijsduijnen, R. Gene 1998, 225, 1.
4. (b) Trowbridge, I. S. Annu. Rev. Immunol. 1994, 12, 85.
5. (c) Neel, B. G. Curr. Opin. Immunol. 1997, 9, 405.
6. Alvi, K. A.; Casey, A.; Nair, B. G. J. Antibiot. 1998, 51, 515.
7. (a) Li, W.-R.; Lin, S. T.; Hsu, N.-M.; Chern, M.-S. J. Org. Chem. 2002, 67, 4702.
8. (b) Bessho, J.; Shimotsu, Y.; Mizumoto, S.; Mase, N.; Yoda, H.; Takabe, K. Heterocycles 2004, 63, 1013.
9. (c) Mangaleswaran, S.; Argade, N. P. Synthesis 2004, 1560.
10. (d) Langlois, N. Synth. Commun. 2006, 36, 2253.
11. (e)Bryans, J. S.; Chessum, N. E. A.; Huther, N.; Parsons, A. F.; Ghelfi, F. Tetrahedron 2003, 59, 6221.
12. Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001.
13. For recent reviews on radical cyclizations, see: (a) Majumdar, K. C.; Basu, K. B.; Chattopadhyay, S. K. Tetrahedron 2007, 63, 793.
14. (b) Rossi, R. A.; Penenory, A. B. Curr. Org. Synth. 2006, 3, 437.
15. (c) Walton, J. C. Top. Curr. Chem. 2006, 264, 163.
16. (a) Clark, A. J. Chem. Soc. Rev. 2002, 31, 1.
17. (b)Nagashima, H.; Itoh, K. J. Synth. Org. Chem., Jpn. 1995, 53, 298.
18. (a) Edlin, C. D.; Faulkner, J.; Helliwell, M.; Knight, C. K.; Parker, J.; Quayle, P.; Raftery, J. Tetrahedron 2006, 62, 3004.
19. (b) De Campo, F.; Lastecoueres, D.; Verlhac, J.-B. Chem. Commun. 1998, 2117.
20. (c) Nagashima, H.; Seki, N.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985.
21. (d) Terent'ev, A. B.; Vasil'eva, T. T.; Kuz'mina, N. A.; Ikonnikov, N. S.; Orlova, S. A.; Mysov, E. I.; Belokon', Y. N. Russ. Chem. Bull. 1997, 46, 2096.
22. (e) Takano, S.; Nishizawa, S.; Akiyama, M.; Ogasawara, K. Heterocycles 1984, 22, 1779.
23. For some typical examples, see: (a) Motoyama, Y.; Hanada, S.; Shimamoto, K.; Nagashima, H. Tetrahedron 2006, 62, 2779.
24. (b) Clark, A. J.; Geden, J. V.; Thorn, S. J. Org. Chem. 2006, 71, 1471.
25. (c) Ghelfi, F.; Parsons, A. F. J. Org. Chem. 2000, 65, 6249.
26. (d) Ghelfi, F.; Bellesia, F.; Forti, L.; Ghirardini, L.; Grandi, R.; Libertini, E.; Montemaggi, M. C.; Pagnoni, U. M.; Pinetti, A.; De Buyck, L.; Parsons, A. F. Tetrahedron 1999, 55, 5839.
27. (e) Benedetti, M.; Forti, L.; Ghelfi, F.; Pagnoni, U. M.; Ronzoni, R. Tetrahedron 1997, 53, 14031.
28. (f) Severin, K. Curr. Org. Chem. 2006, 3, 437.
29. (g) Edlin, C. D.; Faulkner, J.; Quayle, P. Tetrahedron Lett. 2006, 47, 1145.
30. (h) Motoyama, Y.; Hanada, S.; Niibayashi, S.; Shimamoto, K.; Takaoka, N.; Nagashima, H. Tetrahedron 2005, 61, 10216.
31. Felluga, F.; Forzato, C.; Ghelfi, F.; Nitti, P.; Pitacco, G.; Pagnoni, U. M.; Roncaglia, F. Tetrahedron: Asymmetry 2007, 18, 527.
32. (a) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746.
33. (b) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041.
34. (a) Nakano, T.; Nagai, Y. J. Chem. Soc., Chem. Commun. 1981, 815.
35. (b) Zhang, J.; Sarma, K. D.; Curran, T. T. Tetrahedron Lett. 2005, 46, 6433.
36. (a) Haase, C.; Langer, P. Synlett 2005, 453.
37. (b) Jacobi, P. A.; Pippin, D. Org. Lett. 2001, 3, 827.
38. (c) Sam, J.; Lopez, A. V.; Shafik, R. M. J. Pharm. Sci. 1968, 57, 1755.
39. (d) Scheffold, R.; Dubs, P. Helv. Chim. Acta 1967, 50, 798.