Radical-mediated cyclisation of δ-aryl-β-dicarbonyl compounds to β-tetralones [3,4-dihydronaphthalen-2(1H)-ones]

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 21, 1996, Pages 2603-2613

  Jamie, Joanne F ^a   Rickards, Rodney W ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748979551     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960002603     Document Type: Article

References (57)

1. For reviews see: M. Brufani, Top. Antibiot. Chem., 1977, 1, 91;
2. W. Wehrli, Top. Curr. Chem., 1977, 72, 21;
3. K. L. Rinehart, Jr. and L. S. Shield, Fortschr. Chem. Org. Naturst., 1976, 33, 231.
4. For biosynthetic reviews see: O. Ghisalba, Chimia, 1985, 39, 79;
5. O. Ghisalba, J. A. L. Auden, T. Schupp and J. Nüesch, in Biotechnology of Industrial Antibiotics, ed. E. J. Vandamme, Marcel Dekker, New York, 1984, p. 281;
6. G. Lancini, in Biochemistry and Genetic Regulation of Commercially Important Antibiotics, ed. L. C. Vining, Addison-Wesley, London, 1983, p. 231;
7. G. Lancini and M. Grandi, in Antibiotics. Vol. IV. Biosynthesis, ed. J. W. Corcoran, Springer-Verlag, Berlin, 1981, p. 12.
8. J. J. Kibby, I. A. McDonald and R. W. Rickards, J. Chem. Soc, Chem. Commun., 1980, 768;
9. O. Ghisalba, H. Fuhrer, W. J. Richter and S. Moss, J. Antibiot., 1981, 34, 58;
10. O. Ghisalba and J. Nüesch, J. Antibiot., 1981, 34, 64;
11. K. Hatano, S. I. Akiyama, M. Asai and R. W. Rickards, J. Antibiot., 1982, 35, 1415;
12. K. L. Rinehart, Jr., M. Potgieter, W. Jin, C. J. Pearce, D. A. Wright, J. L. C. Wright, J. A. Walter and A. G. McInnes, in Trends in Antibiotic Research. Genetics, Biosynthesis, Actions, and New Substances, ed. H. Umezawa, A. L. Demain, T. Hata and C. R. Hutchinson, Japan Antibiotics Research Association, Tokyo, 1982, p. 171;
13. T. S. Wu, J. Duncan, S. W. Tsao, C. J. Chang, P. J. Keller and H. G. Floss, J. Nat. Prod., 1987, 50, 108;
14. H. G. Floss and J. M. Beale, Angew. Chem., Int. Ed. Engl., 1989, 28, 146.
15. M. G. Anderson, D. Monypenny, R. W. Rickards and J. M. Rothschild, J. Chem. Soc., Chem. Commun., 1989, 311.
16. R. W. Rickards, in Studies in Natural Products Chemistry. Vol. 9, ed. Atta-ur-Rahman, Eisevier Science Publishers B.V., Amsterdam, 1991, p. 431;
17. Proceedings of the Fifth Asian Symposium on Medicinal Plants and Spices, ed. B. H. Han, D. S. Han, Y. N. Han and W. S. Woo, Seoul, 1984, p. 615.
18. A. I. Day, Ph.D. Thesis, Australian National University, Canberra, 1983.
19. (a) A. S. Kende, F. H. Ebetino and T. Ohta, Tetrahedron Lett., 1985, 26, 3063;
20. (b) A. S. Kende, K. Koch and C. A. Smith, J. Am. Chem. Soc., 1988, 110, 2210.
21. (a) B. B. Snider, R. Mohan and S. A. Kates, J. Org. Chem., 1985, 50, 3659;
22. (b) B. B. Snider, R. Mohan and S. A. Kates, Tetrahedron Lett., 1987, 28, 841;
23. (c) R. Mohan, S. A. Kates, M. A. Dombroski and B. B. Snider, Tetrahedron Lett., 1987, 28, 845;
24. (d) B. B. Snider and M. A. Dombroski, J. Org. Chem., 1987, 52, 5487;
25. (e) B. B. Snider, J. J. Patricia and S. A. Kates, J. Org. Chem., 1988, 53, 2137;
26. (f) J. E. Merritt, M. Sasson, S. A. Kates and B. B. Snider, Tetrahedron Lett., 1988, 29, 5209.
27. J. R. Peterson, R. S. Egler, D. B. Horsley and T. J. Winter, Tetrahedron Lett., 1987, 28, 6109.
28. E. J. Corey and M.-C. Kang, J. Am. Chem. Soc., 1984, 106, 5384.
29. A. Citterio, L. Pesce, R. Sebastiano and R. Santi, Synthesis, 1990, 142.
30. A. Citterio, D. Fancelli, C. Finzi, L. Pesce and R. Santi, J. Org. Chem., 1989, 54, 2713.
31. I. S. Aidhen and N. S. Narasimham, Tetrahedron Lett., 1989, 30, 5323;
32. Indian J. Chem, Sect. B, 1993, 32, 222.
33. A. Citterio, A. Cerati, R. Sebastiane, C. Finzi and R. Santi, Tetrahedron Lett., 1989, 30, 1289.
34. D. H. R. Barton, R. D. Bracho, A. A. L. Gunatilaka and D. A. Widdowson, J. Chem. Soc., Perkin Trans. 1, 1975, 579.
35. A. M. Becker, R. W. Rickards and R. F. C. Brown, Tetrahedron, 1983, 39, 4189.
36. W. J. de Klein, in Organic Syntheses by Oxidation with Metal Compounds, ed. W. J. Mijs and C. R. H. I. de Jonge, Plenum Press, New York, 1986, p. 261, and references cited therein.
37. V. Karnojitzky, Russ. Chem. Rev. (Engl. Transl.), 1981, 50, 888.
38. R. van Helden and E. C. Kooyman, Rec. Trav. Chim. Pays-Bas, 1961, 80, 57.
39. B. B. Snider and J. J. Patricia, J. Org. Chem., 1989, 54, 38.
40. D. D. Perrin and W. L. F. Armarego, Purification of Laboratory Chemicals, 3rd Edn, Pergamon Press, Oxford, 1988.
41. M. R. Winkle, J. M. Lansinger and R. C. Ronald, J. Chem. Soc., Chem. Commun., 1980, 87.
42. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.
43. Practical Organic Chemistry: A Student Handbook of Techniques, ed. J. T. Sharp, I. Gosney and A. G. Rowley, Chapman and Hall, London, 1989, p. 160.
44. D. D. Weller, E. P. Stirchak and D. L. Weller, J. Org. Chem., 1983, 48, 4597.
45. A. M. Choudhury, J. Chem. Soc., Perkin Trans. 1, 1974, 132.
46. D. D. Ridley, E. Ritchie and W. C. Taylor, Aust. J. Chem., 1968, 21, 2979.
47. M. Kuchar, B. Brunová, V. Rejholec, Z. Roubal and O. Nemecek, Collect. Czech. Chem. Commun., 1976, 41, 633.
48. R. Huisgen, G. Seidl and I. Wimmer, Liebigs Ann. Chem., 1964, 677, 21.
49. D. C. Appleton, B. Brocklehurst, J. McKenna, J. M. McKenna, S. Thackeray and A. R. Walley, J. Chem. Soc., Perkin Trans. 2, 1980, 87.
50. R. C. Anand and H. Ranjan, Bull. Chem. Soc. Jpn. 1983, 56, 1889.
51. B. Lal, P. Singh, A. P. Bhaduri and K. Kar, Indian J. Chem., 1975, 13, 898.
52. A. K. Sinhababu and R. T. Borchardt, J. Org. Chem., 1983, 48, 2356.
53. J. A. Elix and B. A. Ferguson, Aust. J. Chem., 1978, 31, 1041.
54. P. E. Pfeffer and L. S. Silbert, J. Org. Chem., 1970, 35, 262.
55. P. E. Pfeffer, L. S. Silbert and J. M. Chirinko, Jr., J. Org. Chem., 1972, 37, 451.
56. B. Vu, G. Mezey-Vandor and M. Nogradi, Liebigs Ann. Chem., 1984, 734.
57. N. Katagiri, J. Nakano and T. Kato, J. Chem. Soc., Perkin Trans. 1, 1981, 2710.