Preparation of tetrahydrodibenzocyclooctene lignans and spirodienones by hypervalent iodine oxidation of phenolic dibenzylbutyrolactones

Tetrahedron

Volumn 52, Issue 4, 1996, Pages 1303-1336

  Ward, Robert S ^a   Pelter, Andrew ^a   Abd El Ghani, Atef ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 FURANONE DERIVATIVE; CYCLOALKANE DERIVATIVE; LIGNAN;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030058795     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00960-4     Document Type: Article

References (33)

1. For a preliminary report of this work see, Pelter, A.; Ward, R. S.; Abd-El-Ghani, A., J. Chem. Soc., Perkin Trans. I, 1992, 2249.
2. Pelter, A.; Elgendy, S., J. Chem. Soc., Perkin Trans. I, 1993, 1891.
3. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S., J. Org. Chem., 1992, 57, 2135.
4. Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y., J. Org. Chem., 1987, 52, 3929.
5. Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T., J. Org. Chem., 1991, 56, 435.
6. Rama Krishna, K. V.; Siyatha, K.; Kapil, R. S., Tetrahedron Lett., 1990, 31, 1351.
7. Callinan, A.; Chen, Y.; Harrow, G. W.; Swenton, J. S., Tetrahedron Lett., 1990, 31, 4551.
8. Kita, Y.; Tahma, H.; Iwagaki, M.; Hatanaka, K.; Kikuchi, K.; Yakura, T., Tetrahedron Lett., 1991, 32, 2035.
9. Ayres, D. C.; Loike, J. D., "Lignans: Chemical, Biological and Clinical Properties, Cambridge University Press, 1990, ch. 7.
10. Jackson, D. E.; Dewick, P. M., Phytochem., 1984, 23, 1029 and 1037.
11. Broomhead, A. J.; Rahman, M. M. A.; Dewick, P. M.; Jackson, D. E.; Lucas, J. A., Phytochem., 1991, 30, 1489.
12. Birch, A. J., Liepa A. J., in "Chemistry of Lignans" (ed. C.B.S. Rao), Andhra University Press, India, 1978, ch. 9.
13. Koo, J.; Fish, M. S.; Walker, G. N.; Blake, J., Tetrahedron, 1962, 18, 1063.
14. Palmquist, U.; Nilson, A.; Parker, V. D.; Rolan, A., J. Am. Chem. Soc. 1976, 98, 2571.
15. Pelter, A.; Ward, R. S.; Satyanarayana, P.; Collins, P., J. Chem. Soc., Perkin Trans. 1, 1983, 643.
16. Pelter, A.; Ward, R. S.; Pritchard, M. C.; Kay, I. T., J. Chem. Soc., Perkin Trans. 1, 1988, 1603 and 1615.
17. Truce, W. E.; Roberts, F. E., J. Org. Chem., 1963, 28, 961.
18. Back, T. G.; Yang, K., J. Chem. Soc., Chem. Commun., 1990, 819.
19. Dr. Howarth, O. W., SERC High Field NMR Service, Private Communication.
20. Prof. Hursthouse, H. B., SERC X-ray Crystallography Service, Private Communication.
21. Taafront, M.; Ronessac, F.; Robin, J. P., Tetrahedron Lett., 1983, 24, 197 and 2983.
22. Hicks, R. P.; Sneden, A. T., Tetrahedron Lett., 1983, 24, 2987.
23. Taafront, M.; Rouessac, F.; Robin, J. P., Tetrahedron Lett., 1983, 24, 3237.
24. Carroll, A. R.; Taylor, W. C., Aust. J. Chem., 1990, 43, 1871.
25. Taafront, M.; Rouessac, F.; Robin, J. P.; Davoust, D., Tetrahedron Lett., 1984, 25, 4127.
26. Robin, J. P.; Landais, Y., Tetrahedron, 1992, 48, 819.
27. Pelter, A.; Ward, R. S.; Storer, N. P., Tetrahedron, 1994, 50, 10829.
28. Kofron, W. K.; Baclawski, L. M., J. Org. Chem., 1976, 41, 1879.
29. Watson, S. C.; Eastman, J. F., J. Organometallic Chem., 1967, 9, 165.
30. Brown, H. C., "Organic Synthesis Via Boranes". 1975, Wiley, p. 241.
31. Koo, J.; Fish, M. S.; Walker, G. N.; Blake, J., "Organic Syntheses", Collect. Vol. IV, Wiley, New York, 1963, p 327.
32. Arai, A.; Ichikizaki, I., Bull. Chem. Soc. Japan. 1962, 35, 504.
33. Kashdan, D. S.; Schwanz, J. A.; Rapaport, H., J. Org. Chem., 1982, 47, 2638.