Intramolecular diels-alder reactions of siloxacyclopentene constrained trienes

Organic Letters

Volumn 9, Issue 11, 2007, Pages 2243-2246

  Halvorsen, Geoff T ^a   Roush, William R ^a  

^a Scripps Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; SILOXACYCLOPENTENE; SILOXANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

CYCLOPENTANES; MOLECULAR STRUCTURE; SILOXANES;

EID: 34250639874     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070858u     Document Type: Article

References (44)

1. Ciganek, B. Org. React., 1983, 32, 1.
2. Craig, D. Chem. Soc. Rev., 1986, 16, 187.
3. Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 513-550.
4. Takao, K.; Munakata, R.; Tadano, K. Chem. Rev., 2005, 105, 4779.
5. Boeckman, R. K., Jr.; Barta, T. E. J. Org. Chem., 1985, 50, 3421.
6. (a) Roush, W. R.; Kageyama, M. Tetrahedron Lett., 1985, 26, 4327.
7. (b) Roush, W. R.; Riva, R. J. Org. Chem., 1988, 53, 710.
8. (c) Roush, W. R.; Kageyama, M.; Riva, R.; Brown, B. B.; Warmus, J. S.; Moriarty, K. J. J. Org. Chem., 1991, 56, 1192.
9. Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc., 1998, 120, 7411.
10. Roush, W. R.; Brown, B. B. J. Am. Chem. Soc., 1993, 115, 2268.
11. Frank, S. A.; Roush, W. R. J. Org. Chem., 2002, 67, 4316.
12. Mergott, D. J.; Frank, S. A.; Roush, W. R. Org. Lett., 2002, 4, 3157.
13. (a) Sato, B.; Muramatsu, H.; Miyauchi, M; Hori, Y.; Takase, S.; Hino, M.; Hashimoto, S.; Terano, H. J. Antibiot., 2000, 53, 123.
14. (b) Sato, B.; Nakajima, H.; Hori, Y.; Hino, M.; Hashimoto, S.; Terano, H. J. Antibiot., 2000, 53, 204.
15. (c) Yoshimura, S.; Sato, B.; Kinoshita, T.; Takase, S.; Terano, H. J. Antibiot., 2000, 53, 615.
16. (d) Yoshimura, S.; Sato, B.; Kinoshita, T.; Takase, S.; Terano, H. J. Antibiot., 2002, 55, C-l.
17. (e) Adam, G. C.; Vanderwal, C. D.; Sorensen, E. J.; Cravatt, B. F. Angew. Chem., 2003, 42, 5480.
18. (f) Edler, M. C.; Buey, R. M.; Gussio, R. R.; Marcus, A. I.; Vanderwal, C. D.; Sorensen, E. J.; Diaz, J. F.; Giannakakou, P.; Hamel, E. Biochemistry, 2005, 44, 11525.
19. (a) Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. Org. Lett., 1999, 1, 645.
20. (b) Armstrong, A.; Goldberg, F. W.; Sandham, D. A. Tetrahedron Lett., 2001, 42, 4585.
21. (c) Vanderwal, C. D.; Vosburg, D. A.; Sorensen, E. J. Org. Lett., 2001, 3, 4307.
22. (d) Clarke, P. A.; Davie, R. L.; Peace, S. Tetrahedron Lett., 2002, 43, 2753.
23. (e) Suzuki, T.; Nakada, M. Tetrahedron Lett., 2002, 43, 3263.
24. (f) Methot, J. L.; Roush, W. R. Org. Lett., 2003, 5, 4223.
25. (g) Suzuki, T.; Tanaka, N.; Matsumura, T.; Hosoya, Y.; Nakada, M. Tetrahedron Lett., 2006, 47, 1593.
26. (a) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc., 2002, 124, 4552.
27. (b) Evans, D. A.; Starr, J. T. Angew. Chem., Int. Ed., 2002, 41, 1787.
28. (c) Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. J. Am. Chem. Soc., 2003, 125, 5393.
29. (a) Zacuto, M. J.; O'Malley, S. J.; Leighton, J. L. J. Am. Chem. Soc., 2002, 124, 7890.
30. (b) Clark, T. B.; Woerpel, K. A. J. Am. Chem. Soc., 2004, 126, 9522.
31. (c) Miller, R. L.; Maifeld, S. V.; Lee, D. Org. Lett., 2004, 6, 2773.
32. (d) Trost, B. M.; Ball, Z. T.; Laemmerhold, K. M. J. Am. Chem. Soc., 2005, 127, 10028.
33. (e) Maifeld, S. V.; Lee, D. Org. Lett., 2005, 7, 4995.
34. Tidwell, T. T. Org. React., 1990, 39, 297.
35. (a) Grubbs, R. H. Tetrahedron, 2004, 60, 7117.
36. (b) Thiel, O. R. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 2004; Vol. l, p 321.
37. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed., 2003, 42, 1900.
38. Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem., 2001, 624, 327.
39. Product yields in the absence of benzoquinone were typically <65%. For the use of quinones in metathesis see: Hong, S. H.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc., 2005, 127, 17160.
40. The siloxacyclopentane units of some of the IMDA cycloadducts proved unstable to silica gel chromatography.
41. (a) Oppolzer, W.; Fehr, C.; Warneke, J. Helv. Chim. Acta, 1977, 60, 48.
42. (b) Lin, Y.-T.; Houk, K. N. Tetrahedron Lett., 1985, 26, 2269.
43. (a) Roush, W. R. J. Org. Chem., 1979, 44, 4008.
44. (b) Roush, W. R.; Essenfeld, A. P.; Warmus, J. S. Tetrahedron Lett., 1987, 28, 2447.