Resolution of 7,7-dimethylbicyclo[3.2.0]hept-2-en-6-one using Mortierella ramanniana and 3α,20β-hydroxy-steroid dehydrogenase, photochemistry of 3-hydroxy-7,7-dimethylbicyclo[3.2.0]heptan-6-ones, and the synthesis of (+)-eldanolide

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1987, Pages 903-907

  Butt, Suzanne ^a   Davies, H Geoff ^a   Dawson, Michael J ^a   Lawrence, Gordon C ^a   Leaver, Jeff ^a   Roberts, Stanley M ^a   Turner, Michael K ^a   Wakefield, Basil J ^b   Wall, Wilfred F ^a   Winders, John A ^b  

^a GLAXOSMITHKLINE   (United Kingdom)

^b UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049087366     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19870000903     Document Type: Article

References (27)

1. H. G. Davies, S. M. Roberts, B. J. Wakefield, J. A. Winders, and D. J. Williams, J. Chem. Soc., Chem. Commun., 1984, 640
2. H. G. Davies, S. S. Rahman, S. M. Roberts, B. J. Wakefield, and J. A. Winders, J. Chem. Soc, Perkin Trans. I, 1987, 857
3. E. Lee-Ruff, A. C. Hopkinson, and H. Kazanans-iviognauuaiii, Tetrahedron Lett., 1983, 24, 2062.
4. J. P. Vigneron, R. Meric, M. Larcheveque, A. Debal, J. Y. Lallem, G. Kunesch, P. Zagatti, and M. Gallois, tetrahedron, 1984, 40 3521.
5. For references to other routes to eldanolide see preliminary communication, H. G. Davies, S. M. Roberts, B. J. Wakefield, and J. A. Winders, J. Chem. Soc, Chem. Commun., 1985, 1166
6. E. Dziadulewicz and T. C. Gallagher, Tetrahedron Lett., 1985, 26, 4547
7. H. Frauenrath and T. Philipps, Tetrahedron, 1986, 42, 1135.
8. P. R. Atkinson, J. Entomol. Soc. South Afr., 1980, 43, 171.
9. S. Butt and S. M. Roberts, Nat. Prod. Rep., 1986, 3, 421.
10. M. Rey, S. M. Roberts, A. Dieffenbacher, and A. S. Dreiding, Helv. Chim. Acta, 1970, 43, 417.
11. D. R. Morton, E. Lee-Ruff, R. M. Southam, and N. J. Turro, J. Am. Chem. Soc, 1970, 92, 4349
12. M. Pirrung, Angew. Chem., Int. Ed. Engl., 1985, 24, 1043.
13. I. Kouno and N. Kawano, Chem. Pharm. Bull. (Tokyo), 1983, 4193
14. G. Quinkert, G. Fischer, U. M. Billhardt, J. Glenneberg, H. Hertz, G. Dü nner, E. F. Paulus, and J. W. Bats, Angew. Chem., Int. Ed. Engl, 1984,23,440
15. S. Stiver and P. Yates, Tetrahedron Lett., 1984,25,3289.
16. R. D. Miller, P. Golitz, J. Janssen, and J. Lemmens, J. Am. Chem. Soc, 1984, 106, 7277.
17. M.J. Dawson, G. C. Lawrence, G. Lilley, M. Todd, D. Noble, S. M. Green, S. M. Roberts, T. W. Wallace, R. F. Newton, M. C. Carter, P. Hallett, J. Paton, D. P. Reynolds, and S. Young, J. Chem. Soc, Perkin Trans. 1, 1983, 2119.
18. Preliminary communication; S. Butt, H. G. Davies, M. J. Dawson, C. G. Lawrence, J. Leaver, S. M. Roberts, M. K. Turner, B. J. Wakefield, W. F. Wall, and J. A. Winders, Tetrahedron Lett., 1985, 26, 5077.
19. cf. B. Zhou, A. S. Copalan, F. Van Middlesworth, W. R. Shieh, and C. J. Sih, J. Am. Chem. Soc, 1983, 105, 5925
20. G. Fronza, C. Fuganti, P. Grasselli, and S. Servi, Tetrahedron Lett., 1985, 26, 4961.
21. K. Nakamura, K. Ushio, S. Oka, and A. Ohno, Tetrahedron Lett., 1984, 25, 3979
22. T. Kitazume and N. Ishikawa, Chem. Lett., 1983, 237.
23. J. B. Jones in ‘Enzymes in Organic Synthesis,’ Ciba Foundation Symposium III eds. R. Porter, and S. Clark, Pitman, London, 1985, p. 3.
24. D. D. Perrin, W. L. F. Armarego, and D. R. Perrin, ‘Purification of Laboratory Chemicals,’ Pergamon, Oxford, 1980.
25. W. C. Still, M. Kahn, and A. Mitra, J. Org. Chem., 1978, 43, 2923.
26. Z. Grudzinski and S. M. Roberts, J. Chem. Soc, Perkin Trans 1,1975, 1767.
27. J. M. Berge and S. M. Roberts, Synthesis, 1979, 471.