Diastereoselective SmI2-mediated cascade radical cyclisations of methylenecyclopropane derivatives - A synthesis of paeonilactone B

Chemical Communications

Volumn , Issue 17, 1998, Pages 1875-1876

  Boffey, Raymond J ^a   Santagostino, Marco ^a   Whittingham, William G ^b   Kilburn, Jeremy D ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002496942     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804297g     Document Type: Article

References (19)

1. M. Malacria, Chem. Rev., 1996, 96, 289.
2. 2 have been reported. Two notable examples are:
3. (b) T. L. Fevig, R. L. Elliott and D. P. Curran, J. Am. Chem. Soc., 1988, 110, 5064;
4. R. A. Batey, J. D. Marling and W. B. Motherwell, Tetrahedron, 1996, 52, 11 421.
5. T. Hayashi, T. Shinbo, M. Shimizu, M. Arisawa, N. Monta, M. Kimura, S. Matsuda and T. Kikuchi, Tetrahedron Lett., 1985, 26, 3699.
6. For previous syntheses of paeonilactones see: M. Rönn, P. G. Andersson and J.-E. Bäckval, Acta Chem. Scand., 1998, 52, 524;
7. S. Hatakeyama, M. Kawamura, Y. Mukugi and H. Irie, Tetrahedron Lett., 1995, 36, 267 and references cited therein.
8. For previous studies on cyclisations of methylenecyclopropylalkyl radicals see: C. Destabel, J. D. Kilburn and J. Knight, Tetrahedron, 1994, 38, 11 267;
9. M. Santagostino and J. D. Kilburn, Tetrahedron Lett., 1995, 36, 1365 and references cited therein.
10. T. Oishi, M. Nagai and Y. Ban, Tetrahedron Lett., 1968, 491.
11. 13C NMR and IR spectroscopy, and by HRMS or microanalysis.
12. We thank Dr M. Webster, University of Southampton, for carrying out the X-ray crystallographic analysis. Details will be published elsewhere.
13. G. A. Molander and J. A. McKie, J. Org. Chem., 1995, 60, 872.
14. 2-mediated cyclisations of unactivated olefinic ketones, see: G. A. Molander and J. A. McKie, J. Org. Chem., 1992, 57, 3132. See also ref. 2b.
15. 2-mediated cyclisations of unactivated olefinic ketones: see refs. 10 and 2(b).
16. C. H. Heathcock, S. D. Young, J. P. Hagen, R. Pilli and U. Badertscher, J. Org. Chem., 1985, 50, 2095.
17. T. J. Brocksom, R. B. dos Santos, N. A. Varanda and U. Brocksom, Synth. Commun., 1988, 18, 1403.
18. D. J. Cram and C. A. Kingsbury, J. Am. Chem. Soc., 1960, 82, 1810.
19. D. Boschelli, T. Takemasa, Y. Nishitani and S. Masamune, Tetrahedron Lett., 1985, 26, 5239.