Synthesis of vinyl spirolactones and lactams by sequential cross- coupling metathesis, [2+2] photocycloaddition and cyclobutane ring-opening

Tetrahedron Letters

Volumn 40, Issue 33, 1999, Pages 6001-6004

  Faure, Sophie ^a   Blanc, Sylvie Piva Le ^a   Piva, Olivier ^a,b  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

Allyltrimethylsilane; Cyclobutane; Metathesis; Spirolactam; Spirolactone

Indexed keywords

CYCLOBUTANE; LACTAM; SPIRONOLACTONE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; IRRADIATION; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0033551753     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01173-9     Document Type: Article

References (32)

1. (a) Comins, D. L.; Zhang, Y.-m.; Zheng, X. Chem. Commun. 1998, 2509-2510.
2. (b) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B. J. Am. Chem. Soc. 1999, 121, 4900-4901 and references therein.
3. François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 104-105.
4. Le Blanc, S.; Pete, J.-P.; Piva, O. Tetrahedron Lett. 1992, 33, 1993-1996.
5. Dugar, S.; Clader, J. W.; Chan, T. M.; Davis Jr, H. J. Med. Chem. 1995, 38, 4875-4877.
6. Piva, O. Unpublished results.
7. Crimmins, M. T.; Rheingold, T. L. In Org. Reactions; Paquette, L. A., Ed.; John Wiley: New York, 1993; Vol. 44, pp. 298-588.
8. (a) Le Blanc, S.; Pete, J.-P.; Piva, O. Tetrahedron Lett. 1993, 34, 635-638.
9. (b) Faure, S.; Piva-Le Blanc, S.; Piva, O.; Pete, J.-P. Tetrahedron Lett. 1997, 38, 1045-1048.
10. (a) Ochiai, M.; Arimoto, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1981, 460-461.
11. (b) Pirrung, M. C.; Webster, N. J. G. J. Org. Chem. 1987, 52, 3603-3613.
12. (a) Fujiwara, T.; Suda, A.; Takeda, T. Chem. Lett. 1991, 1619-1622.
13. (b) Fujiwara, T.; Suda, A.; Takeda, T. Chem. Lett. 1992, 1631-1634.
14. (c) Fujiwara, T.; Sawabe, K.; Takeda, T. Tetrahedron 1997, 53, 8349-8370.
15. Lange, G. L.; Furlan, L.; MacKinnon, M. C. Tetrahedron Lett. 1998, 39, 5489-5492 .
16. Reviews: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2057.
17. (b) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, 1997.
18. (c) Fürstner, A. Topics in Catalysis 1997, 4, 285-299.
19. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
20. (e) Pariya, C.; Jayaprakash, K. N.; Sarkar, A. Coord. Chem. Rev. 1998, 168, 1-48.
21. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
22. For recent works on metathesis of allylsilanes: (a) Marciniec, B.; Foltynowicz, Z.; Lewandowski, M. J. Mol. Catal. 1994,90, 125-133.
23. (b) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120.
24. (c) Schuster, M.; Lucas, N.; Blechert, S. Chem. Commun. 1997, 823-824.
25. (d) Meyer, C.; Cossy, J. Tetrahedron Lett. 1997, 38, 7861-7864.
26. (e) Cassidy, J. H.; Marsden, S. P.; Stemp, G. Synlett 1997, 1411-1413.
27. (f) Blanco, O. M.; Castedo, L. Synlett 1999, 557-558.
28. Fleming, I.; Barbero, A.; Walter, D. Chem Rev. 1997, 97, 2063-2192.
29. (a) White, J. D.; Ruppert, J. F.; Avery, M. A.; Torii, S.; Nokami, J. J. Am. Chem. Soc. 1981, 103, 1813-1821.
30. (b) Cainelli, G.; Contento, M.; Manescalchi, F.; Plessi, L. Synthesis 1989, 47-48.
31. Baldwin, J. E.; Barden, T. C.; Pugh, R. L.; Widdison, W. C. J. Org. Chem. 1987, 52, 3303-3307.
32. +--28).