Extended π-Participation in Biomimetic Cyclization of Squalene Derivatives

Croatica Chemica Acta

Volumn 69, Issue 4, 1996, Pages 1347-1359

  Borčić, Stanko ^a   Humski, Krešimir ^a   Kronja, Olga ^a   Malnar, Ivica ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005821607     PISSN: 00111643     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (48)

1. (a) R. B. Clayton, Quart. Rev. Chem. Soc. (London) 19 (1965) 168-200;
2. (b) E. J. Corey, W. E. Russey, and P. R. Ortiz de Montellano, J. Am. Chem. Soc. 88 (1966) 4750;
3. (c) E. J. Corey and W. E. Russey, J. Am. Chem. Soc. 88 (1966) 4751;
4. (d) E. E. van Tamelen, J. D. Willet, R. B. Clayton, and K. E. Lord, J. Am. Chem. Soc. 88 (1966) 4752;
5. (e) L. J. Mulheirn and P. J. Ramm, Chem. Soc. Rev. 1 (1972) 259-291.
6. (a) E. E. van Tamelen, J. D. Willet, M. Schwartz, and R. Nadeau, J. Am. Chem. Soc. 88 (1966) 5937-5938;
7. (b) E. E. van Tamelen and D. R. James, J. Am. Chem. Soc. 99 (1977) 950.
8. For reviews, see: (a) P. A. Stadler, A. Nechvatal, A. J. Frey, and A. Eschenmoser, Helv. Chim. Acta 40 (1957) 1373;
9. (b) H. Dugs and C. Penney, Bioorganic Chemistry, Springer-Verlag, New York, 1981, pp. 318-328;
10. (c) P. A. Bartlett, in: J. D. Morrison (Ed.), Asymmetric Syntheses, Academic Press, New York, 1985, Vol. 3, pp. 341-409.
11. For reviews, see: (a) W. S. Johnson, Acc. Chem. Res. 8 (1968) 1-8;
12. (b) W. S. Johnson, Bioorg. Chem. 5 (1976) 51-98;
13. (c) W. S. Johnson, Angew. Chem., Int. Ed. Engl. 15 (1976) 9-17.
14. (a) W. S. Johnson, S. J. Telfer, S. Cheng, and U. Schubert, J. Am. Chem. Soc. 109 (1987) 2517-2518;
15. (b) W. S. Johnson, S. D. Lindell, and J. Steele, J. Am. Chem. Soc. 109 (1987) 5852-5853;
16. (c) D. Guay, W. S. Johnson, and U. Schubert, J. Org. Chem. 54 (1989) 4731-4732.
17. For reviews, see: (a) E. E. van Tamelen, Acc. Chem. Res. 1 (1968) 111-120;
18. (b) E. E. van Tamelen, Acc. Chem. Res. 8 (1975) 152-158.
19. E. E. van Tamelen, J. Am. Chem. Soc. 104 (1982) 6480-6481.
20. S. Borčić, O. Kronja, and K. Humski, Croat. Chem. Acta 67 (1994) 171-188.
21. (a) E. Polla, S. Borčić, and D. E. Sunko, Tetrahedron Lett. (1975) 799-802;
22. (b) I. Mihel, M. Orlović, E. Polla, and S. Borčić, J. Org. Chem. 44 (1979) 4086-4090.
23. (a) M. Orlović, E. Polla, and S. Borčić, J. Org. Chem. 48 (1983) 2278-2280;
24. (b) M. Orlović, K. Humski, S. Borčić, and E. Polla, J. Chem. Soc., Chem. Commun. (1986) 263-264;
25. (c) M. Orlović, S. Borčić, K. Humski, O. Kronja, V. Imper, E. Polla, and V. J. Shiner, Jr., J. Org. Chem. 56 (1991) 1874-1878.
26. O. Kronja, E. Polla, and S. Borčić, J. Chem. Soc., Chem. Commun. (1983) 1044-1045.
27. S. Borčić, K. Humski, V. Imper, O. Kronja, M. Orlović, and E. Polla, J. Chem. Soc., Perkin Trans, 1 (1989) 1861.
28. H. Nan-hui and W. J. le Noble, J. Org. Chem. 54 (1989) 2018-2021.
29. O. Kronja, M. Orlović, K. Humski, and S. Borčić, J. Am. Chem. Soc. 113 (1991) 2306-2308.
30. I. Malnar, O. Kronja, K. Humski, and S. Borcic, Croat. Chem. Acta 65 (1992) 547-549.
31. O. Kronja, S. Borčić, K. Humski, and C. S. Foote, Croat. Chem. Acta 63 (1990) 193-202.
32. (a) C. J. Lancelot and P. von R. Schleyer, J. Am. Chem. Soc. 91 (1969) 4291-4294;
33. (b) J. M. Harris, F. L. Schadt, P. von R. Schleyer, and C. J. Lancelot, J. Am. Chem. Soc. 91 (1969) 7508-7510.
34. For reviews, see: (a) H. H. Jaffe, Chem. Rev. 53 (1953) 191;
35. (b) H. C. Brown and Y. Okamoto, J. Am. Chem. Soc. 80 (1958) 4979;
36. (c) L. P. Hammett, Physical Organic Chemistry, 9, Interscience, New York, 1972.;
37. (d) M.-F. Ruasse, A. Argile, and J.-E. Dubois, J. Am. Chem. Soc. 106 (1984) 4846-4849.
38. D. J. Hupe and W. P. Jencks, J. Am. Chem. Soc. 99 (1977) 451-464.
39. (a) P. G. Gassman and A. F. Fentiman, Jr., J. Am. Chem. Soc. 92 (1970) 2549-2551;
40. (b) H. Tanida and T. Tsushima, J. Am. Chem, Soc. 92 (1970) 3397-3403;
41. (c) E. N. Peters, J. Am. Chem. Soc. 98 (1976) 5627-5632;
42. (d) H. C. Brown, The Non-Classical Ion Problem, Plenum Press, New York, 1977.
43. (a) A. Pross, Adv. Phys. Org. Chem. 14 (1977) 69-132;
44. (b) C. D. Johnson, Tetrahedron 36 (1980) 3461-3480.
45. O. Exner, Collect. Czech. Chem. Commun. 31 (1966) 3222.
46. (a) P. G. Gassman, J. Zeller, and J. T. Lumb, Chem. Commun. (1968) 69-71;
47. (b) P. G. Gassman and A. F. Fentiman, Jr., J. Am. Chem. Soc. 91 (1969) 1545-1546.
48. D. S. Noyce and R. M. Pollack, J. Am. Chem. Soc. 91 (1969) 119.