Spiroannulation of a cyclopentane ring. Synthesis of spiro[4.n](n+5)alk-2-en-1-ones

Journal of the Indian Chemical Society

Volumn 76, Issue 11-12, 1999, Pages 521-526

  Srikrishna, A ^a   Kumar, P Praveen ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013215975     PISSN: 00194522     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (37)

1. R. A. Ellison, Synthesis, 1973, 397;
2. T. A. Kametani and N. Fukumoto, Heterocycles, 1978, 10, 469;
3. L. A. Paquette, Top. Curr. Chem., 1979, 79, 41;
4. B. M. Trost, Chem. Soc. Rev., 1979, 79, 41;
5. L. A. Paquette, Top. Curr. Chem., 1984, 119, 1;
6. M. Ramaiah, Synthesis, 1984, 529;
7. L. A. Paquette and A. M. Doherty, "Recent Developments in Polyquinane Chemistry", Springer-Verlag, 1987;
8. N. E. Schore, Chem. Rev., 1989, 89, 1467;
9. N. E. Schore in "Comprehensive Organic Synthesis", eds. B. M. Trost and I. Fleming, Pergamon, New York, 1991, Vol. 5;
10. G. Piancatelli, M. D'Auria and F. D'Onofrio, Synthesis, 1994, 867;
11. G. Mehta and A. Srikrishna, Chem. Rev., 1997, 671;
12. V. Singh and B. Thomas, Tetrahedron, 1998, 54, 3647.
13. (a) J. A. Marshall, S. F. Brady and N. H. Anderson,Fortschr. Chem. Org. Naturst., 1974, 31, 283;
14. (b) C. H. Heathcock, S. L. Graham, M. C. Pirrung, F. Plavac and C. T. White in "The Total Synthesis of Natural Products", ed. J. Apsimon, Wiley, New York, 1983, Vol. 5;
15. (c) J. Jonas, V. Herout and F. Sorm,Collect. Czech. Chem. Commun., 1964, 29, 539;
16. (d) W. Fenical and B. M. Howard, Tetrahedron Lett., 1968, 2483;
17. (e) J. A. Marshall and P. C. Johnson, J. Org. Chem., 1970, 35, 192;
18. (f) A. Stoessl, J. B. Stothers and E. W. B. Ward, Can. J. Chem., 1975, 431;
19. (g) F. Bohlmann and J. Jakupovic, Phytochemistry, 1980, 19, 259;
20. (h) P. Naegeli and R. Kaiser, Tetrahedroin Lett., 1972, 2009;
21. (i) P. S. Rao, K. G. Sarma and T. R. Seshadri, Curr. Sci., 1965, 34, 9;
22. P. S. Rao, K. G. Sarma and T. R. Seshadri, Curr. Sci., 1966, 35, 147;
23. (j) M. Maruyama, A. Terahara, Y. Itagaki and K. Nakanishi, Tetrahedron Lett., 1967, 299;
24. (k) R. L. Ranieri and G. J. Calton, Tetrahedron Lett., 1978, 499.
25. For preliminary communication, see ; A. Srikrishna, T. J. Reddy, P. P. Kumar and D. Vijaykumar, Synlett, 1996, 67.
26. (a) L. Claisen, Chem. Ber., 1912, 45, 3157;
27. (b) C. R. Holmquist and E. J. Roskamp, J. Org. Chem., 1989, 54, 3258;
28. (c) J. E. McMurry and L. C. Blaszczak, J. Org. Chem., 1974, 39, 2217;
29. (d) F. E. Ziegler, Acc. Chem. Res., 1977, 10, 227;
30. (e) G. B. Bennett, Synthesis, 1977, 589;
31. (f) R. P. Lutz, Chem. Rev., 1984, 84, 205;
32. (g) F. E. Ziegler, Chem. Rev., 1988, 88, 1423.
33. J. Tsuji, I. Shimizu and K. Yamamoto, Tetrahedron Lett., 1976, 2975.
34. (a) J. Tsuji, I. Shimizu and Y. Kobayashi, Isr. J. Chem., 1984, 24, 153;
35. (b) M. Pohmakotr and P. Phinyocheep, Tetrahedron Lett., 1984, 25, 2249.
36. A. Srikrishna and T. J. Reddy, Tetrahedron, 1998, 54, 8133.
37. A. Srikrishna, D. Vijaykumar and T. J. Reddy, Tetrahedron, 1997, 53, 1439.