Cascade radical cyclisations leading to polycyclic diterpenes. Total synthesis of (±)-spongian-16-one

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 5, 1998, Pages 863-868

  Pattenden, Gerald ^a   Roberts, Lee ^a   Blake, Alexander J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748600689     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a708042e     Document Type: Article

References (34)

1. G. Cimino, R. Morrone and G. Sodano, Tetrahedron Lett., 1982, 23, 4139.
2. M. R. Kernan, R. C. Cambie and P. R. Bergquist, J. Nat. Prod., 1990, 53, 724.
3. T. W. Hambley, A. Poiner and W. C. Taylor, Aust. J. Chem., 1990, 43, 1861.
4. A. G. Gonzalez, D. M. Estrada, J. D. Martin, V. S. Martin, C. Perez and R. Perez, Tetrahedron, 1984, 40, 4109.
5. S. Kohmoto, O. J. McConnell, A. Wright and S. Cross, Chem. Lett., 1987, 168;
6. R. Kazauskas, P. T. Murphy, R. J. Wells, K. Noack, W. E. Oberhansli and P. Schonoholzer, Aust. J. Chem., 1919, 32, 867.
7. T. Nakano and M. I. Hernández, Tetrahedron Lett., 1982, 1423;
8. D. S. de Miranda, G. Brendolan, P. M. Imamura, M. González-Sierra, A. J. Marsaioli and E. A. Rúveda, J. Org. Chem., 1981, 46, 4851;
9. P. M. Imamura, M. González-Sierra and E. A. Rúveda, J. Chem. Soc., Chem. Commun., 1981, 734;
10. T. Nakano, M. I. Hernández, M. Gomez and J. D. Medina, J. Chem. Res. Synop., 1989, 54;
11. M. G. Sierra, M. P. Mischne and E. A. Rúveda, Synth. Commun., 1985, 15, 27;
12. T. Sakamoto and K. Kanematsu, Tetrahedron, 1995, 51, 5771.
13. For studies of oxidative radical cyclisations of polyenes and applications to the synthesis of (±)-isospongiadiol see: P. A. Zoretic, M. Wang, Y. Zhang and Z. Shen, J. Org. Chem., 1996, 61, 1806 and references cited therein.
14. L. Chen, G. B. Gill, G. Pattenden and H. Simonian, J. Chem. Soc., Perkin Trans. 1, 1996, 31;
15. A. Batsanov, L. Chen, G. B. Gill and G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 1996, 45 and references cited therein.
16. P. Double and G. Pattenden, unpublished work.
17. G. Pattenden and L. Roberts, Tetrahedron Lett., 1996, 37, 4191.
18. S. Hatakeyama, H. Numata, K. Osanai and S. Takano, J. Chem. Soc., Chem. Commun., 1989, 1893;
19. cf. G. Cahiez, A. Alexakis and J. F. Normant, Tetrahedron Lett., 1978, 3013;
20. S. A. Godleski, D. J. Heacock, J. D. Meinhart and S. Van Wallendael, J. Org. Chem., 1983, 48, 2101;
21. S. A. Stanton, S. W. Felman, C. S. Parkhurst and S. A. Godleski, J. Am. Chem. Soc., 1983, 105, 19.
22. W. S. Johnson, R. A. Buchanan, W. R. Bartlett, F. S. Tham and R. K. Knullnig, J. Am. Chem. Soc., 1993, 115, 504.
23. M. Julia, S. Julia and R. Guegan, Bull. Soc. Chim. Fr., 1960, 1072.
24. K. Iwai, H. Kosugi, H. Uda and M. Kawai, Bull. Chem. Soc. Jpn., 1977, 50, 242.
25. B. M. Trost, M. K.-T. Mao, J. M. Balkovec and P. Buhlmayer, J. Am. Chem. Soc., 1986, 108, 4965.
26. K. C. Nicolaou, N. A. Petasis and D. A. Claremon, Tetrahedron, 1985, 41, 4835.
27. L. Lombardo, Org. Synth., 1987, 81.
28. P. A. Wender and S. L. Eck, Tetrahedron Lett., 1982, 1871;
29. B. M. Trost and H. Hiemstra, J. Am. Chem. Soc., 1982, 104, 886;
30. W. Oppolzer and T. Godel, J. Am. Chem. Soc., 1978, 100, 2583.
31. 3).
32. G. M. Sheldrick, SHELXS-86, Acta Crystallogr., Sect. A, 1990, 46, 467.
33. G. M. Sheldrick, SHELXL-93, University of Göttingen, Germany, 1993.
34. G. M. Sheldrick, SHELXTL/PC, version 5.03, Siemens Analytical Instruments Inc., Madison, WI, 1995.