Enyne versus diene RCM in the synthesis of cyclopentene derivatives toward the A ring of FR182877

Journal of Organic Chemistry

Volumn 69, Issue 13, 2004, Pages 4555-4558

  Funel, Jacques Alexis ^a   Prunet, Joëlle ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; SYNTHESIS (CHEMICAL);

CYCLOPENTENE DERIVATIVES; METATHESIS; RING SIZE;

ORGANIC COMPOUNDS;

ALKADIENE; ANTINEOPLASTIC AGENT; CYCLOPENTENE DERIVATIVE; FR 182877; UNCLASSIFIED DRUG; WS 9885B;

ARTICLE; CATALYSIS; CATALYST; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

ALKADIENES; CYCLOPENTANES; MOLECULAR CONFORMATION; POLYCYCLIC COMPOUNDS;

EID: 3042744115     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049557d     Document Type: Article

References (35)

1. Sato, B.; Muramatsu, H.; Miyauchi, M.; Hori, Y.; Takese, S.; Hino, M.; Hashimoto, S.; Terano, H. J. Antibiot. 2000, 53, 123.
2. Yoshimura, S.; Sato, B.; Kinoshita, T.; Takese, S.; Terano, H. J. Antibiot. 2000, 53, 615.
3. Yoshimura, S.; Sato, B.; Kinoshita, T.; Takese, S.; Terano, H. J. Antibiot. 2002, 55, C-1.
4. Sato, B.; Nakajima, H.; Hori, Y.; Hino, M.; Hashimoto, S.; Terano, H. J. Antibiot. 2000, 53, 204.
5. (a) Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. Org. Lett. 1999, 1, 645.
6. (b) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552.
7. (c) Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. J. Am. Chem. Soc. 2003, 125, 5393.
8. (a) Evans, D. A.; Starr, J. T. Angew. Chem., Int. Ed. 2002, 41, 1787.
9. (b) Evans, D. A.; Starr, J. T. J. Am. Chem. Soc. 2003, 125, 13531.
10. Suzuki, T.; Nakada, M. Tetrahedron Lett. 2002, 43, 3263.
11. Armstrong, A.; Goldberg, F. W.; Sandham, D. A. Tetrahedron Lett. 2001, 42, 4585.
12. Methot, J. L.; Roush, W. R. Org. Lett. 2003, 5, 4223.
13. A similar reaction has been reported by Takano for the synthesis of estrone: Takano, S.; Moriya, M.; Ogasawara, K. Tetrahedron Lett. 1992, 33, 1909.
14. For a recent review on enyne metathesis, see: Poulsen, C. S.; Madsen, R. Synthesis 2003, 1.
15. Evans, D. A.; Gage, J. R. Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434.
16. (a) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009.
17. (b) Mohr, P. Tetrahedron Lett. 1991, 32, 2219.
18. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
19. (b) P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100.
20. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
21. Mori, M.; Sakakira, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082.
22. (a) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674.
23. (b) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247.
24. (c) Jafarpour, L.; Hillier, A. C.; Nolan, S. P. Organometallics 2002, 21, 442.
25. (a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000,122, 8168.
26. (b) Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973.
27. Aubert, C.; Buisine, O.; Malacria, M. Chem Rev. 2002, 102, 813 and references therein.
28. Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441.
29. Dolhem, F.; Lièvre, C.; Demailly, G. Eur. J. Org. Chem. 2003, 2336.
30. Preparation of compounds 11a-c is described in the Supporting Information.
31. Preparation of compounds 13a-c is described in the Supporting Information.
32. For similar RCM reactions on carbohydrate-derived dienes, see: Hyldtoft, L.; Madsen, R. J. Am. Chem. Soc. 2000, 122, 8444.
33. Hoye has shown that free allylic hydroxyl groups have a large activating effect on diene RCM: Hoye, T. R.; Zhao, H. Org. Lett. 1999, 1, 1123.
34. Stork, G.; Paterson, I.; Lee, F. K. C. J. Am. Chem. Soc. 1982, 104, 4686.
35. Paquette, L. A.; Schloss, J. D.; Efremov, I.; Fabris, F.; Gallou, F.; Méndez-Andino, J.; Yang, J. I. Org Lett. 2000, 2, 1259.