Synthesis of multi-substituted furan rings: the role of silicon

Abstract

Silanes have proven extremely useful for the synthesis of multi-substituted furan rings. Their judicious placement on a furan ring can be used to control either the placement of new groups around the furan ring or the silane can be directly replaced via an ipso-substitution. This paper will briefly review the role silicon has played in the preparation of furan rings having a variety of substituent patterns.

References

1. B. A. Keay and P. W. Dibble, in Comprehensive Heterocyclic Chemistry II, ed., C. W. Bird, Elsevier, New York, 1996, vol. 2, ch. 2.08, pp. 395–436.
2. X. L. Hou, H. Y. Cheung, T. Y. Hon, P. L. Kwan, T. H. Lo, S. Y. Tong and H. N. C. Wong, Tetrahedron, 1998, 54, 1955 and references therein.
3. R. A. Benkeser and R. B. Currie, J. Am. Chem. Soc., 1948, 70, 1780.
4. A. J. Carpenter and D. J. Chadwick, Tetrahedron Lett., 1985, 26, 1777.
5. D. W. Knight and A. P. Nott, J. Chem. Soc., Perkin Trans. 1, 1983, 791.
6. D. J. Chadwick, M. V. McKnight and R. Ngochindo, J. Chem. Soc., Perkin Trans. 1, 1982, 1343.
7. D. S. Ennis and T. L. Gilchrist, Tetrahedron Lett., 1990, 46, 2623.
8. J.-Y. Lenoir, P. Ribereau and G. Queguiner, J. Chem. Soc., Perkin Trans. 1, 1994, 2943.
9. E. Bures, P. G. Spinazze, G. Beese, I. R. Hunt, C. Rogers and B. A. Keay, J. Org. Chem., 1997, 62, 8741.
10. E. Bures, J. A. Nieman, S. Yu, P. G. Spinazze, J.-L. J. Bontront, I. R. Hunt, A. Rauk and B. A. Keay, J. Org. Chem., 1997, 62, 8750.
11. R. E. Danso-Danquah, A. I. Scott and D. Becker, Tetrahedron, 1993, 49, 8195.
12. J. A. Nieman and B. A. Keay, Tetrahedron Lett., 1994, 35, 5335.
13. E. J. Bures and B. A. Keay, Tetrahedron Lett., 1988, 29, 1247.
14. S. Katsumura, K. Ichikawa and H. Mori, Chem. Lett., 1993, 1525.
15. R. L. Beddoes, M. L. Lewis, P. Gilbert, P. Quayle, S. P. Thompson, S. Wang and K. Mills, Tetrahedron Lett., 1996, 37, 9119.
16. B. A. Keay and J.-L. Bontront, Can. J. Chem., 1991, 69, 1326.
17. W. A. Cristofoli and B. A. Keay, Tetrahedron Lett., 1991, 32, 5881.
18. S. P. Maddaford and B. A. Keay, J. Org. Chem., 1994, 59, 6501.
19. S. P. Maddaford, N. G. Andersen, W. A. Cristofoli and B. A. Keay, J. Am. Chem. Soc., 1996, 118, 10766.
20. K. Nakayama, Y. Harigaya, H. Okamoto and A. Tanaka, J. Heterocycl. Chem., 1991, 28, 853.
21. K. Nakayama and A. Tanaka, Chem. Pharm. Bull., 1992, 40, 1966.
22. K. Nakayama and A. Tanaka, Chem. Express, 1991, 6, 699.
23. M. S. Ho and H. N. C. Wong, J. Chem. Soc., Chem. Commun., 1989, 1238.
24. Z. Z. Song, Z. Y. Zhou, T. C. W. Mak and H. N. C. Wong, Angew. Chem., Int. Ed. Engl., 1993, 32, 432.
25. Z. Z. Song, M. S. Ho and H. N. C. Wong, J. Org. Chem., 1994, 59, 3917.
26. Z. Zhong and H. N. C. Wong, J. Org. Chem., 1994, 59, 33.
27. Z. Z. Song and H. N. C. Wong, Liebigs Ann. Chem., 1994, 29.
28. M. K. Wong, C. Y. Leung and H. N. C. Wong, Tetrahedron, 1997, 53, 3497.
29. Z. Z. Song and H. N. C. Wong, J. Chin. Chem. Soc., 1995, 42, 673.
30. I. Kuwajima and H. Urabe, Tetrahedron Lett., 1981, 22, 5191.
31. D. Goldsmith, D. Liotta, M. Saindane, L. Waykole and P. Brown, Tetrahedron Lett., 1983, 24, 5835.
32. S. P. Tannis and D. Head, Tetrahedron Lett., 1984, 25, 4451.
33. W. Adam and A. Rodriguez, Tetrahedron Lett., 1981, 22, 3505.
34. S. Katsumura, K. Hori, S. Fujiwara and S. Isoe, Tetrahedron Lett., 1985, 26, 4625 and Tetrahedron Lett., 1988, 29, 1173.
35. Y. Hatanaka, S. Fukushima and T. Hiyama, Tetrahedron, 1992, 48, 2113 and references therein.