Functionalised pyrrolidinones derived from (S)-pyroglutamic acid by cycloaddition reactions

Tetrahedron

Volumn 53, Issue 34, 1997, Pages 11731-11744

  Bailey, Jonathan H ^a   Cherry, David T ^a   Crapnell, Katherine M ^a   Moloney, Mark G ^a   Shim, Sung Bo ^a   Bamford, Mark J ^b   Lamont, R Brian ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0030743398     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00740-0     Document Type: Article

References (40)

1. Massiot, G.; Delaude, C. The Alkaloids 1986, 27, 300-321.
2. Wink, M. The Alkaloids 1993, 43, 1-118.
3. Thottathil, J. K.; Przbyla, C.: Malley, M.; Gougoutas, J. Z. Tetrahedron Lett. 1986, 27, 1533-1536.
4. Thottathil, J. K.; Moniot, J. M.; Mueller, R. H.; Wong, M. K. Y.; Kissick, T. P. J. Org. Chem. 1986, 51, 3140-3143.
5. Baldwin, J. E.; Moloney, M. G.; Shim, S. B. Tetrahedron Lett. 1991, 32, 1379-1380.
6. Beard, M. J.; Bailey, J. H.; Cherry, D. T.; Moloney, M. G.; Shim, S. B.; Statham, K.; Bamford, M.; Lamont, R. B. Tetrahedron 1996, 52, 3719-3740 and corrigenda 1997, 53, 1177.
7. Hamada, Y.; Hara, O.; Kawai, A.; Ohno, Y.; Shiori, T. Tetrahedron 1991, 47, 8635-8652.
8. Hanessian, S.; Ratovelomanana, V. Synlett. 1991, 222-224.
9. Armstrong, R. W.; DeMattei, J. A. Tetrahedron Lett. 1991, 32, 5749-5752.
10. Griffart-Brunet, D.; Langlois, N. Tetrahedron Lett. 1994, 35, 119-122.
11. Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron:Asymmetry 1994, 5, 119-128.
12. Nagasaka, T.; Imai, T. Chem. Pharm. Bull. 1995, 43, 1081-1088.
13. For a preliminary account, see: Bamford, M.; Beard, M.; Cherry, D. T.; Moloney, M. G. Tetrahedron: Asymmetry 1995, 6, 337-340.
14. Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8.
15. Busacca, C. A.; Meyers, A. I. J. Chem. Soc., Perkin Trans. 1 1991, 2299-2316.
16. Fray, A. H.; Meyers, A. I. Tetrahedron Lett. 1992, 33, 3575-3578.
17. Fray, A. H.; Meyers, A. I. J. Org. Chem. 1996, 61, 3362-3374.
18. Reich, H. J.; Renga, J. M.; Reich, I. L. J. Am. Chem. Soc. 1975, 97, 5434-5437.
19. Dyer, J.; Keeling, S.; Moloney, M. G. Tetrahedron Lett. 1996, 37, 4573-4576.
20. Nagasaka, T.; Imai, T. Heterocycles 1995, 41, 1927-1930.
21. Nagasaka, T.; Imai, T. Chem. Pharm. Bull. 1997, 45, 36-42.
22. Grote, R.; Zeeck, A.; Stumpfel, J.; Zahner, H. Liebigs Ann. Chem. 1990, 525-530.
23. Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511-3513.
24. Ackarmann, J.; Matthes, M.; Tamm, C. Helv. Chim. Acta 1990, 71, 122-132 and references there-in.
25. Ezquerra, J.; Pedregal, C.; Collado, I.; Yruretagoyena, B.; Rubio, A. Tetrahedron 1995, 57, 10107-10114.
26. Danishevsky, S.; Hirama, M.; Gombatz, K.; Harayama, T.; Berman, E.; Schuda, P. F. J. Am. Chem. Soc. 1979, 7022-7028.
27. Brownbridge, P. Synthesis 1983, 85-104.
28. Danishevsky, S. Acc. Chem. Res. 1981, 14, 400.
29. Koot, W. J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1992, 57, 1059-1061.
30. Rispens, M. T.; Keller, E.; deLange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron:Asymmetry 1994, 5, 607-624.
31. Wee, A. G. H. J. Chem. Soc., Perkin Trans. 1 1989, 1363-1364.
32. Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Deyine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 57, 3571-3586.
33. Houk, K. N.; Sims, J.; Duke, R. E.; Strozier, R. W.; George, J. K. J. Am. Chem. Soc. 1973, 95, 7287-7301.
34. Houk, K. N.; Sims, J.; Watts, C. R.; Luskus, L. J. J. Am. Chem. Soc. 1973, 95, 7301-7315.
35. Atomic Coordinates have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from Cambridge Crystallographic Data Centre, 12 Union Rd, Cambridge. CB2 1EZ, U.K.
36. Vedejs, E.; Campbell, J. B.; Gadwood, R. C.; Rodgers, J. D.; Spear, K. L.; Watanabe, Y. J. Org. Chem. 1982, 47, 1534-1546.
37. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
38. Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748.
39. Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746-749.
40. Harwood, L. M.; Manage, A. C.; Robin, S.; Hopes, S. F. G.; Watkin, D.; Williams, C. E. SynLett. 1993, 10, 777-780.