Acyl radical-mediated polyene cyclisations directed towards steroid ring synthesis

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 1, 1996, Pages 45-55

  Batsanov, Andrei ^a   Chen, Ligong ^a   Gill, G Bryon ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542735945     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960000045     Document Type: Article

References (23)

1. L. Chen, G. B. Gill, G. Pattenden and H. Simonian, J. Chem. Soc., Perkin Trans. 1, 1996, immediately preceding paper;
2. preliminary communication: L. Chen, G. B. Gill and G. Pattenden, Tetrahedron Lett., 1994, 35, 2593.
3. J. K. Whitesell and M. A. Minton, Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy, Chapman and Hall, London, 1987.
4. D. K. Dalling and D. M. Grant, J. Am. Chem. Soc., 1974, 96, 1827;
5. F. W. Wehrli and T. Wirthlin, Interpretation of C-13 NMR Spectra, Heyden, London 1976, p. 44.
6. T. Terasawa, Y. Yoshimura and K. Tori, J. Chem. Soc., Perkin Trans. 1, 1983, 903.
7. For contemporaneous studies of radical mediated approaches to steroid ring constructions see details in ref. 1, and also P. A. Zoretic, Z. Shen, M. Wang and A. A. Ribeiro, Tetrahedron Lett., 1995, 36, 2925;
8. T. Takahashi, W. Katouda, Y. Sakamoto, S. Tomida and H. Yamada, Tetrahedron Lett., 1995, 36, 2273.
9. W. Oppolzer, K. Bättig and T. Hudlicky, Tetrahedron, 1981, 37, 4359.
10. J. Tsuji, K. Masaoka, T. Takahashi, A. Suzuki and N. Miyaura, Bull. Chem. Soc. Jpn., 1977, 50, 2507.
11. H. J. Bestmann, K. M. Koschatzky and O. Vostrowsky, Liebigs Ann. Chem., 1982, 1478.
12. P. A. Zoretic, X. Weng and M. L. Caspar, Tetrahedron Lett., 1991, 32, 4819;
13. P. A. Zoretic, M. Ramchandani and M. L. Caspar, Synth. Commun., 1991, 21, 915.
14. R. I. Trust and R. E. Ireland, Org. Synth., 1973, 53, 116.
15. R. E. Ireland, T. C. McKenzie and R. I. Trust, J. Org. Chem., 1975, 40, 1007.
16. E. S. Rao and J. S. Yadav, Indian J. Chem., Sect. B, 1986, 25, 1174.
17. W. S. Johnson, L. Werthemann, W. R. Bartlett, T. J. Brocksom, T.-t. Li, D. J. Faulkner and M. R. Petersen, J. Am. Chem. Soc., 1970, 92, 741;
18. W. S. Johnson, S. J. Telfer, S. Cheng and U. Schubert, J. Am. Chem. Soc., 1987, 109, 2517.
19. Cf. W. S. Johnson, B. Chenera, F. S. Tham and R. K. Kullnig, J. Am. Chem. Soc., 1993, 115, 493.
20. A. V. Semenovski, V. L. Mizyuk, V. N. Odinokov, V. R. Akhunova and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1981, 821
21. (Chem. Abstr., 1981, 95, 98053d).
22. G. U. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467.
23. G. U. Sheldrick, SHELXL-93, University of Göttingen, Germany, 1993.